Ethanol → HCID 13731134, compound

HRID 3839Notes

Reaction equation

HRID 3839 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26]Cl)[CH2:20][CH2:19]2)=[CH:10][CH:9]=1.C(O)C.[OH-].[Na+]>O>[ClH:7].[ClH:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][SH:3])[CH2:20][CH2:19]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 13731112HCID 13731112, compound

Product 1

HCID 13731134HCID 13731134, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 1.0 g of thiourea, 4.0 g of 1-[4-(4-chlorophenyl)butyl]-4-(3-chloropropyl)piperazine dihydrochloride and 50 ml of reagent ethanol. The hydrolysis was effected with 4.0 g of sodium hydroxide in 50 ml of water. Work-up of the free base, as described above followed by purification on a silica gel column (methylene chloride:methanol, 97:3), precipitation as the hydrochloride salt and recrystallization from reagent ethanol, gave 0.6 g (16% of theory) of 3-{4-[4-(4-chlorophenyl)butyl]piperazin-1-yl}propanethiol dihydrochloride as a white crystalline solid, M.p. 254°-259° C.

Workup

  1. customabove followed by purification on a silica gel column (methylene chloride:methanol, 97:3), precipitation as the hydrochloride salt and recrystallization from reagent ethanol

Sources & evidence

ORD record
ord-bf5cd469793a4ce49e0abb6aa996f1d7
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Reaction notes

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