Triethylamine → 2-[4-(4-Chlorobenzyl)piperazin-1-yl]ethanethiol dihydrochloride

HRID 3833Notes

Reaction equation

HRID 3833 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[Cl:7][C:8]1[CH:23]=[CH:22][C:11]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20]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:23]=[CH:22][C:11]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][SH:3])[CH2:15][CH2:14]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 123621271-(4-Chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochloride

Product 1

HCID 201531732-[4-(4-Chlorobenzyl)piperazin-1-yl]ethanethiol dihydrochlorideYield 97.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 6.1 g of thiourea, 13.8 g of 1-(4-chlorobenzyl)-4-(2-chloroethyl)piperazine dihydrochloride, 4.1 g of triethylamine and 150 ml of reagent ethanol. The hydrolysis was effected with 7.0 g of sodium hydroxide and 50 ml of water. Work-up, as described above, gave 6.7 g (62% of theory) of 2-[4-(4-chlorobenzyl)piperazin-1-yl]ethanethiol dihydrochloride as a white crystalline solid, M.p. 244°-247° C.

Sources & evidence

ORD record
ord-a44d77395f1c48f3a29b906d95127ca1
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Reaction notes

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