Phenethyl bromide → HCID 3028311, compound

HRID 1388796Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][CH2:14]Br)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:32]=[C:31]([C:33](=[O:41])[CH2:34][CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1>CN(C)C=O>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:32]=[C:31]([C:33](=[O:41])[CH2:34][CH:35]3[CH2:36][CH2:37][N:38]([CH2:14][CH2:13][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH2:39][CH2:40]3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3.45 g of potassium carbonate and 1.39 g of 2-phenylethyl bromide are added to a solution of 1.72 g of 1-[2-(4-methyl-phenyl)-4-quinolyl]-2-(4-piperidyl)-ethanone, prepared as indicated in Example 8, in 25 ml of dimethylformamide. The suspension, well stirred, is heated for 5 hours at 60° C., then poured into 1 liter of ice-water. The oil which separates is decanted, washed with water, then 100 ml of ether and 100 ml of a 1 N aqueous solution of hydrochloric acid are added. The precipitate formed is filtered, washed with water and then with acetone. 2 g of 1[2-(4-methyl-phenyl)-4-quinolyl]-2-[1-(2-phenyl-ethyl)-4-piperidyl]-ethanone are obtained in the form of dihydrochloride melting at 195° C.

Workup

customprepared
customThe oil which separates is decanted
washwashed with water
addition100 ml of ether and 100 ml of a 1 N aqueous solution of hydrochloric acid are added
customThe precipitate formed
filtrationis filtered
washwashed with water

Sources & evidence

ORD record: ord-a156f5e4e22940028b8e95f1cbb49d2a
Source dataset: uspto-grants-1984_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04433150

Reaction notes

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