Triethylamine → 3-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propanethiol dihydrochloride

HRID 3828Notes

Reaction equation

HRID 3828 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][N:17]2[CH2:22][CH2:21][N:20]([C:23]3C=CC=[C:25](Cl)[CH:24]=3)[CH2:19][CH2:18]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:7].[ClH:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][SH:3])[CH2:19][CH2:18]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 201531861-[3-(4-Chlorophenyl)propyl]-4-(3-chlorophenyl)piperazine dihydrochloride

Product 1

HCID 137311303-{4-[3-(4-Chlorophenyl)propyl]piperazin-1-yl}propanethiol dihydrochlorideYield 134.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 7.6 g of thiourea, 22.9 g of 1-[3-(4-chlorophenyl)propyl]-4-(3-chlorophenyl)piperazine dihydrochloride, 5.8 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 10.0 g of sodium hydroxide in 50 ml of water. Work-up, as described above, gave 14.1 g (65% of theory) of 3-{4-[3-(4-chlorophenyl)propyl]piperazin-1-yl}propanethiol dihydrochloride as a white crystalline solid, M.p. 238°-242° C.

Sources & evidence

ORD record
ord-25a33070dbbc46b2856cae32c57e7fb1
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Reaction notes

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