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

HRID 3808

Reaction equation

HRID 3808 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[CH3:7][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:22])[CH2:15][CH2:14]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:22].[ClH:5].[CH3:7][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 201531921-(4-Methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 137311203-[4-(4-Methylbenzyl)piperazin-1-yl]propanethiol dihydrochlorideYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 7.7 g of thiourea, 23.0 g of 1-(4-methylbenzyl)-4-(3-chloropropyl)piperazine dihydrochloride, 6.5 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 described above, gave 16.4 g (72% of theory) of 3-[4-(4-methylbenzyl)piperazin-1-yl]propanethiol dihydrochloride as a white crystalline solid, M.p. 273°-277° C. (dec.).

Sources & evidence

ORD record
ord-76581291372d4210a560be5a42ab7838
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Linked notes

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