Sodium Hydroxide → 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[4-(1-methylethyl)aminobutyl]phenoxy]ethyl]piperazine trihydrochloride

HRID 2418012Notes

Reaction equation

HRID 2418012 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]Cl)[CH2:21][CH2:20]3)[C:4]=2[CH:3]=1.[CH3:28][CH:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)[CH3:30].[OH-].[Na+]>O>[ClH:1].[ClH:1].[ClH:1].[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[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][O:42][C:39]4[CH:40]=[CH:41][C:36]([CH2:35][CH2:34][CH2:33][CH2:32][NH:31][CH:29]([CH3:28])[CH3:30])=[CH:37][CH:38]=4)[CH2:23][CH2:24]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 52754552-Chloro-10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]phenothiazineHCID 20446958HCID 20446958, compound

Product 1

HCID 133384751-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[4-(1-methylethyl)aminobutyl]phenoxy]ethyl]piperazine trihydrochlorideYield 127.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-(2-chloroethyl)piperazine (10 g) and 4-[4-(1-methylethyl)aminobutyl]phenol (4.9 g) was stirred at 55° under nitrogen and a solution of sodium hydroxide (0.94 g) in water (7 ml) was added. The reaction was stirred and heated at 55°-65° for 5 hours. The usual work-up yielded the crude trihydrochloride salt. Crystallization of the product from methanol-ethanol yielded 5.3 g of 1-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-4-[2-[4-[4-(1-methylethyl)aminobutyl]phenoxy]ethyl]piperazine trihydrochloride, mp 245°-248°.

Workup

  1. temperatureheated at 55°-65° for 5 hours
  2. customThe usual work-up yielded the crude trihydrochloride salt
  3. customCrystallization of the product from methanol-ethanol

Sources & evidence

ORD record
ord-4d7a565a87c84608b6d852583cb8a031
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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