2,2-Diphenylacetyl chloride → HCID 69686920, compound

HRID 1070750Notes

Reaction equation

Cl.Cl.Cl.[N:4]1([CH2:10][CH2:11][NH:12][C:13](=[O:22])[CH:14]=[CH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[C:23]1([CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[C:33]1([CH:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:30]([N:7]2[CH2:8][CH2:9][N:4]([CH2:10][CH2:11][NH:12][C:13](=[O:22])[CH:14]=[CH:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH2:5][CH2:6]2)=[O:31])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 0 °C

Procedure

8.0 g (22.6 mmol) N-[2-(piperazin-1-yl)-ethyl]-3-pyridin-3-yl-acrylic amide trihydrochloride (substance 317 as a trihydrochloride) and 13 ml (92.7 mmol) TEA are present in 100 ml absolute dichloromethane and cooled to ca. 0° C. under moisture exclusion. 6.3 g (24.9 mmol) diphenylacetyl chloride (90%) are dissolved in 70 ml absolute dichloromethane and added dropwise. The mixture is stirred overnight at RT without further cooling. Subsequently, 200 ml dichloromethane are added and the batch is washed three times each with 100 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is crystallized twice from 40 ml and 30 ml acetonitrile. Beige coloured crystals of MP. 1740° C. yield 4.6 g (44%).

Workup

additionadded dropwise
washthe batch is washed three times each with 100 ml water
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is removed under vacuum
customThe residue is crystallized twice from 40 ml and 30 ml acetonitrile
customcrystals of MP. 1740° C. yield 4.6 g (44%)

Sources & evidence

ORD record: ord-56c1d9aa602e4d26bcddb4d5ab5ed563
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903118B1

Reaction notes

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