Perphenazine → 2-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazine

HRID 2417972Notes

Reaction equation

HRID 2417972 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26]O)[CH2:21][CH2:20]3)[C:4]=2[CH:3]=1.C(N(CC)CC)C.S([Cl:39])(C)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][Cl:39])[CH2:21][CH2:20]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 4748PerphenazineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[3-(2-chlorophenothiazin-10-yl)propyl]-1-piperazineethanol (22.5 g) was added to 186 ml of dry dichloromethane containing triethylamine (7.8 ml). The stirred solution was cooled to -10° and maintained at that temperature during the dropwise addition of a solution of 5.1 ml of mesyl chloride in 50 ml of dry dichloromethane. The ice bath was then removed and the reaction was stirred overnight at room temperature. The solution was washed with 25 ml of a 5% sodium bicarbonate solution and then dried over anhydrous potassium carbonate. The solvent was removed in vacuo (bath temperature, 25°) to yield 24.2 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4(2-chloroethyl)piperazine 2a as an oil.

Workup

  1. temperatureThe stirred solution was cooled to -10°
  2. customThe ice bath was then removed
  3. washThe solution was washed with 25 ml of a 5% sodium bicarbonate solution
  4. dry with materialdried over anhydrous potassium carbonate
  5. customThe solvent was removed in vacuo (bath temperature, 25°)

Sources & evidence

ORD record
ord-61a5df7d467d4983a1125e135c82155a
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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