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

HRID 3813

Reaction equation

HRID 3813 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[C:7]1([CH:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][Cl:24])[CH2:17][CH2:16]2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:24].[ClH:5].[C:7]1([CH:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][SH:3])[CH2:17][CH2:16]2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 201531701-(1-Phenylethyl)-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 137311223-[4-(1-Phenylethyl)piperazin-1-yl]propanethiol dihydrochlorideYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 9.8 g of thiourea, 29.0 g of 1-(1-phenylethyl)-4-(3-chloropropyl)piperazine dihydrochloride, 8.3 g of triethylamine and 250 ml of reagent ethanol. The hydrolysis was effected with 6.0 g of sodium hydroxide in 40 ml of water. Work-up, as above, gave 14.5 g (51% of theory) of 3-[4-(1-phenylethyl)piperazin-1-yl]propanethiol dihydrochloride as a white crystalline solid, M.p. 252°-255° C.

Sources & evidence

ORD record
ord-d017d716638549a595ea280009b45216
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Linked notes

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