(4-Fluorophenoxy)acetyl chloride → 1-[2-(4-Fluorophenoxy)ethyl]-4-(9-fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine

HRID 1389288Notes

Reaction equation

HRID 1389288 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]3[CH:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[CH:20]=[CH:21][C:8]=3[S:7][C:6]=2[CH:25]=1.[F:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](Cl)=O)=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([N:12]3[CH2:13][CH2:14][N:15]([CH2:33][CH2:32][O:31][C:30]4[CH:36]=[CH:37][C:27]([F:26])=[CH:28][CH:29]=4)[CH2:16][CH2:17]3)[C:9]3[CH:18]=[C:19]([CH:22]([CH3:23])[CH3:24])[CH:20]=[CH:21][C:8]=3[S:7][C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 2759057(4-Fluorophenoxy)acetyl chlorideHCID 41250111-(9-Fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine

Product 1

HCID 46218011-[2-(4-Fluorophenoxy)ethyl]-4-(9-fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2.6 g of 3-fluoro-8-isopropyl-10-piperazino-10,11-dihydrodibenzo(b,f)thiepin in 15 ml of chloroform was stirred and treated dropwise with 1.7 g of 4-fluorophenoxyacetyl chloride and the mixture allowed to stand for 12 hours. It was then diluted with chloroform, washed with a 5% sodium hydroxide solution and water, dried with potassium carbonate, filtered and evaporated. The oily residue (3.7 g, 100%) was the crude 3-fluoro-10-[4-(4-fluorophenoxyacetyl)-piperazino]-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin which was used in this state for further work.

Workup

  1. washwashed with a 5% sodium hydroxide solution and water
  2. dry with materialdried with potassium carbonate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-603e82a1c16e4bbbb05198838fd21409
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

Loading…