Formaldehyde → N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)(methyl)amino]-1-phenylethyl]carbamic acid tert-butyl ester

HRID 32463Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]=O>>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][N:10]([CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]([CH3:19])[CH3:20])[CH2:16][CH2:17]1)[CH3:28])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 712Formaldehyde

HCID 69307988N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)amino]-1-phenyl-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 69310514N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)(methyl)amino]-1-phenylethyl]carbamic acid tert-butyl esterYield 98%

Procedure

Using alkylation method B, N-[(R)-2-[(1-isopropyl-piperidin-4-ylmethyl)amino]-1-phenylethyl]carbamic acid tert-butyl ester (511 mg, 1.4 mmol) and paraformaldehyde (816 mg, 27 mmol) afforded 522 mg (98%) of the title compound as a crude residue that was used without further purification.

Sources & evidence

ORD record: ord-d528d99cb90e443ba64545e70e4a690f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427632B2

Reaction notes

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