Triethylamine → HCID 21440886, compound

HRID 329050Notes

Reaction equation

HRID 329050 reaction equation
C[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:3](Cl)=[O:4].[F:11][C:12]([F:42])([F:41])[C:13]1[CH:26]=[CH:25][C:24]2[S:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][C:33]([O:37][CH2:38][CH2:39][OH:40])([CH3:36])[CH2:32][CH2:31]3)[C:15]=2[CH:14]=1.[CH2:43](N(CC)CC)C>C1C=CC=CC=1>[F:42][C:12]([F:41])([F:11])[C:13]1[CH:26]=[CH:25][C:24]2[S:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][C:33]([O:37][CH2:38][CH:39]([CH3:43])[O:40][C:3](=[O:4])[CH2:2][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])([CH3:36])[CH2:34][CH2:35]3)[C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2181082-Trifluoromethyl-10-[3-(4-{2-hydroxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazineHCID 142345192-Methylheptanoyl chloride

Product 1

HCID 21440886HCID 21440886, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.7 g of 2-methylheptanoic acid chloride in 10ml of anhydrous benzene was added dropwise at 10° C to a solution of 6.05 g of 2-trifluoromethyl-10-[3-(4-{2-hydroxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine in 50 ml of anhydrous benzene containing 1.7 g of triethylamine and the mixture was stirred at room temperature for 20 hours. After washing the benzene solution with water, the mixture was stirred for 4 hours with an aqueous solution saturated with sodium bicarbonate and the organic phase was decanted and concentrated.. The oily residue was purified by chromatography over silica gel with a 99-1 cyclohexane-triethylamine mixture as eluant to obtain 6.5 g of 2-trifluoromethyl-10-[3-(4-{2-methyl -2-heptanoyloxyethoxy}-4-methyl-piperidino)-propyl]-phenothiazine in the form of a yellow oil.

Workup

  1. washAfter washing the benzene solution with water
  2. stirringthe mixture was stirred for 4 hours with an aqueous solution saturated with sodium bicarbonate
  3. customthe organic phase was decanted
  4. concentrationconcentrated
  5. customThe oily residue was purified by chromatography over silica gel with a 99-1 cyclohexane-triethylamine mixture as eluant

Sources & evidence

ORD record
ord-6dce5fa9a7ad4150b347d80e6141ec04
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

Loading…