Water → [4-(3,3-diphenyl-propionyl)-piperazin-1-yl]-acetic Acid Ethyl Ester

HRID 456428Notes

Reaction equation

[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][C:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:14]1[CH2:13][CH2:12][N:11]([C:9](=[O:10])[CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:16][CH2:15]1)[CH3:29]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3,3-diphenyl-1-piperazin-1-yl-propan-1-one (2.0 g, 6.79 mmol) and ethyl bromoacetate (0.94 ml, 8.49 mmol) in dry DMF (15 ml) was added K2CO3 (2.7 g, 19.53 mmol) and the mixture was heated to 70° C. overnight. Reaction mixture was cooled and water (32 ml) was added. The product was extracted with ether, dried and evaporated. The residue was purified by column chromatography using hexane:ethyl acetate (1:4) to give the desired product in 60% yield.

Workup

customReaction mixture
temperaturewas cooled
extractionThe product was extracted with ether
customdried
customevaporated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-50da0476aa054ee9a44d38c410468735
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186726B2

Reaction notes

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