(4-BROMOBENZYL)METHYLAMINE

Preparation of (4-Bromo-benzyl)-methyl-amineMeNHIn an autoclave, a mixture of 4-bromobenzaldehyde (2.08 g, 11.15 mmol) and methylamine 2M solution in methanol (25 mL, 33.44 mmol) was stirred at 65° C. for 4 h. After cooling to rt, sodium borohydride (633 mg, 16.72 mmol) was added portionwise. The reaction mixture was stirred at rt for 30 min, then concentrated in vacuo. The resulting residue was dissolved in EA (30 mL) and the organic layer washed with a sat. NaHCOTo a solution of i-bromo-4-(bromoinethyl)benzene (5.00 g, 20.0 mrnol) in TI-IF (30 rnL) was added 2M methylamine in THF (100 mL, 200.0 mmol) and the reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture WaS diluted with 1.5 N HCI solution (50 rnL) extracted with ethyl acetate (3 x 30 mL). The aqueousextract was basified with NaFICOs and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain Intermediate 17A (3.50 g. 870percent). ‘H NMR (400 MHz, DMSO-d6) S ppm 2.26 (s, 3 H), 363 (s, 2 H), 7.24 - 7.32 (m, 2 H), 7.47 7.54 (m. 2 H), (Exchangeable proton not observed) LCMS (Method—i):retention time 0.68 mm, (M+H) 201.0.Step (vii) of Reference 1-(4-Bromophenyl)-N-methylmethanamine 4-Bromobenzyl bromide (200 mg, 0.800 mmol) was added slowly to a 2 M solution (4 ml) of methanamine in tetrahydrofuran, and the solution was stirred at room temperature for 24 hr. The reaction solution was adjusted to pH 3 by the addition of 1 N hydrochloric acid and was then washed twice with diethyl ether. A saturated aqueous sodium hydrogencarbonate solution was added to the aqueous layer, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure to give 136.1 mg (yield 85percent) of the title compound.

Molecular Weight:200.08
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:198.99966
Monoisotopic Mass:198.99966
Topological Polar Surface Area:12
Heavy Atom Count:10
Complexity:87.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes