Triethylamine → 3-(4-Cinnamylpiperazin-1-yl)propanethiol dihydrochloride

HRID 3842Notes

Reaction equation

HRID 3842 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[CH2:7]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][Cl:25])[CH2:18][CH2:17]1)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:25].[ClH:5].[CH2:7]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][SH:3])[CH2:18][CH2:17]1)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 704154971-Cinnamyl-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 731868363-(4-Cinnamylpiperazin-1-yl)propanethiol dihydrochlorideYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 3.1 g of thiourea, 7.4 g of 1-cinnamyl-4-(3-chloropropyl)piperazine dihydrochloride, 4,1 g of triethylamine and 100 ml of reagent ethanol. The hydrolysis was effected with 3.0 g of sodium hydroxide in 30 ml of water. Work-up, as described above, gave 3.6 g (52% of theory) of 3-(4-cinnamylpiperazin-1-yl)propanethiol dihydrochloride as a white crystalline solid, M.p. 249°-252° C.

Sources & evidence

ORD record
ord-c7de0e9fa1d24e82a534bc829b4771d1
Source dataset
uspto-grants-1988_02
Patent number
US04722926

Reaction notes

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