Triethylamine → {5-[4-(4-Methoxy-benzyl)-2,2-dimethyl-piperazin-1-ylmethyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

HRID 43142

Reaction equation

HRID 43142 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2([CH3:22])[CH3:21])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=3)[CH2:17][C:16]2([CH3:22])[CH3:21])=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1650214-Methoxybenzyl bromideHCID 66914635[5-(2,2-Dimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 66914558{5-[4-(4-Methoxy-benzyl)-2,2-dimethyl-piperazin-1-ylmethyl]-pyridin-2-yl}-carbamic acid tert-butyl esterYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [5-(2,2-dimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (Step 109.3) (3.85 g, 12 mmol), 4-methoxybenzyl bromide (2.6 mL, 18 mmol, 1.5 equiv) and triethylamine (1.83 mL, 13.2 mmol, 1.1 equiv) in DCM (25 mL) was stirred for 16 h at it and concentrated. The residue was purified by silica gel column chromatography (DCM DCM/MeOH, 97:3) to afford 1.88 g of the title compound as a white solid. Title compound: ESI-MS: 441.3 [M+H]+; tR=3.12 min (System 1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (DCM DCM/MeOH, 97:3)

Sources & evidence

ORD record
ord-f2f3dc44d99f4bd3ada726d6c99e3623
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

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