Triethylamine → 3-[4-(4-Chlorobenzyl)piperazin-1-yl]propanethiol dihydrochloride

HRID 3793

Reaction equation

HRID 3793 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21]Cl)[CH2:15][CH2:14]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:24]=[CH:23][C:11]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][SH:3])[CH2:15][CH2:14]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 201531894-Chlorobenzyl-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 137311183-[4-(4-Chlorobenzyl)piperazin-1-yl]propanethiol dihydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Utilizing the procedure described in Example 1(b), 6.0 g of thiourea, was reacted with 25.2 g of 1-(4-chlorobenzyl-4-(3-chloropropyl)piperazine dihydrochloride and 8.7 g of triethylamine in 200 ml of reagent ethanol. The hydrolysis was effected with 5.0 g of sodium hydroxide in 50 ml of water. Work-up as described above gave 16.6 g (75% of theory) of 3-[4-(4-chlorobenzyl)piperazine-1-yl]propanethiol dihydrochloride as an off-white crystalline solid, M.p. 257°-260° C.

Sources & evidence

ORD record
ord-dd78e8a69cf04d3fa6ac7e292bbcdfdd
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Linked notes

Loading…