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

HRID 2290873
Notes
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Reaction equation

HRID 2290873 reaction equation
NC(N)=[S:3].[ClH:5].Cl.[CH2:7]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][Cl:24])[CH2:17][CH2:16]1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[ClH:24].[ClH:5].[CH2:7]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][SH:3])[CH2:17][CH2:16]1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 201531791-Phenethyl-4-(3-chloropropyl)piperazine dihydrochloride

Product 1

HCID 137311243-(4-Phenethylpiperazin-1-yl)propanethiol dihydrochlorideYield 81.6%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

The procedure described in Example 1(b) was followed, using 15.2 g of thiourea, 32.6 g of 1-phenethyl-4-(3-chloropropyl)piperazine dihydrochloride, 20.0 g of triethylamine and 250 ml of reagent ethanol The hydrolysis was effected with 10.0 g of sodium hydroxide in 40 ml of water. Work-up, as described above, gave 26.4 g (79% of theory) of 3-(4-phenethylpiperazin-1-yl)propanethiol dihydrochloride as an off-white crystalline solid, M.p. 269°-272° C.

Sources & evidence

ORD record
ord-da3c67e0d34b4311af46b8b83e33b12f
Source dataset
uspto-grants-1986_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04618677

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes