Formaldehyde → 1-(4-Bromo-3-methoxyphenyl)-4-methylpiperazine

HRID 908394Notes

Reaction equation

[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[O:15][CH3:16].[CH2:17](N(C(C)C)C(C)C)C.C=O>ClCCl>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH3:17])[CH2:13][CH2:14]2)=[CH:5][C:4]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 25 °C

Procedure

Sodium triacetoxyhydroborate (25.9 mg) was added to 1-(4-bromo-3-methoxy-phenyl)piperazine (30 mg), N-ethyl-N-isopropyl-propan-2-amine (0.030 ml) and 37% aqueous formaldehyde (8.01 μl) dissolved in dichloromethane (1 ml). The resulting mixture was stirred at 25° C. for 2 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate (5 ml) and extracted with ethyl acetate (2×10 ml). The combined organic phases were dried over magnesium sulfate and concentrated to afford the crude 1-(4-bromo-3-methoxy-phenyl)-4-methyl-piperazine (25.00 mg). NMR Spectrum: (CDCl3) 2.38 (s, 3H), 2.60 (bs, 4H), 3.17-3.28 (m, 4H), 3.88 (s, 3H), 6.41 (dd, 1H), 6.47 (d, 1H), 7.36 (d, 1H); Mass spectrum: M+H+ 286

Workup

customThe reaction mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate (5 ml)
extractionextracted with ethyl acetate (2×10 ml)
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-041bc44b223c423dae19d64e76485d0b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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