Triethylamine → 3-(2,2'-dichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamide

HRID 1785646Notes

Reaction equation

HRID 1785646 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH:5]([O:13][CH:14]1[CH2:17][NH:16][CH2:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12].[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:5]([O:13][CH:14]1[CH2:17][N:16]([C:27]([NH:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:15]1)[C:4]1[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=1[Cl:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 689078523-(2,2'-Dichlorobenzhydryloxy)azetidine hydrochloride

Product 1

HCID 689024333-(2,2'-dichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) (0.29 mmol), tert-butyl isocyanate (0.29 mmol) and triethylamine (0.58 mmol) in dichloromethane (3 mL) was shaken at room temperature overnight, quenched with water, filtered through a PTFE phase separator cartridge and reduced in vacuo to yield a colourless gum (52 mg, 44%).

Workup

  1. customquenched with water
  2. filtrationfiltered through a PTFE phase separator cartridge

Sources & evidence

ORD record
ord-30fb082b0b2e449a9dd68e4718af7da1
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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