Ethyl isocyanate → N-(1-Boc-piperidin-3-yl-methyl)-N-phenyl-N'-ethylurea

HRID 1016545Notes

Reaction equation

HRID 1016545 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:25]([NH:24][CH2:22][CH3:23])=[O:26])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 12972131N-(1-Boc-piperidin-3-ylmethyl)aniline

Product 1

HCID 12972132N-(1-Boc-piperidin-3-yl-methyl)-N-phenyl-N'-ethylureaYield 95%

Procedure

To a solution of N-(1-Boc-piperidin-3-ylmethyl)aniline 1 (102 mg, 0.35 mmol) in 1 mL of dry CH2Cl2was added ethyl isocyanate (95%, 35 μL, 1.2 eq.) at room temperature. After being shaken at room temperature for overnight, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2. Removal of the CH2Cl2 afforded N-(1-Boc-piperidin-3-yl-methyl)-N-phenyl-N′-ethylurea (2) (120 mg, 95%). LRMS 285 (M-100)+ 261.

Workup

  1. washwashed with CH2Cl2
  2. customRemoval of the CH2Cl2

Sources & evidence

ORD record
ord-edf865da5b9a422baf18473828b938ac
Source dataset
uspto-grants-2002_11
Patent number
US06476050B2

Reaction notes

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