Palmitoyl chloride → 2-Trifluoromethyl-10-[3-(4-{2-hexadecanoyloxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine

HRID 329051Notes

Reaction equation

HRID 329051 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[F:19][C:20]([F:50])([F:49])[C:21]1[CH:34]=[CH:33][C:32]2[S:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH2:35][CH2:36][CH2:37][N:38]3[CH2:43][CH2:42][C:41]([O:45][CH2:46][CH2:47][OH:48])([CH3:44])[CH2:40][CH2:39]3)[C:23]=2[CH:22]=1.C(N(CC)CC)C>C1C=CC=CC=1>[F:49][C:20]([F:19])([F:50])[C:21]1[CH:34]=[CH:33][C:32]2[S:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH2:35][CH2:36][CH2:37][N:38]3[CH2:39][CH2:40][C:41]([O:45][CH2:46][CH2:47][O:48][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([CH3:44])[CH2:42][CH2:43]3)[C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 2181082-Trifluoromethyl-10-[3-(4-{2-hydroxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine

Product 1

HCID 214409172-Trifluoromethyl-10-[3-(4-{2-hexadecanoyloxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazineYield 84.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3.3 g of hexadecanoic acid chloride in 20 ml of anhydrous benzene was added dropwise at 10° C to a solution of 5 g of 2-trifluoromethyl-10-[3-(4-{2-hydroxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine in 50 ml of anhydrous benzene containing 1.2 g of triethylamine and the mixture was stirred for 20 hours at room temperature. The mixture was washed with water and then was stirred for 4 hours with 100 ml of an aqueous saturated sodium bicarbonate solution. The organic phase was decanted and concentrated. The oily residue was subjected to chromatography over silica gel with a 98-2 benzene-triethylamine mixture as eluant to obtain 6.4 g of 2-trifluoromethyl-10-[3-(4-{2-hexadecanoyloxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine in the form of a yellow oil.

Workup

  1. washThe mixture was washed with water
  2. stirringwas stirred for 4 hours with 100 ml of an aqueous saturated sodium bicarbonate solution
  3. customThe organic phase was decanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbb7cbc825c74b8a83faa455ea90c579
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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