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Piperidine → Phenylmethyl alpha-[[[2-(diethylamino)ethyl]thio]methyl]benzenepropanoate

HRID 375842
Notes
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Reaction equation

HRID 375842 reaction equation
[CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][SH:26])[CH3:22].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][S:26][CH2:1][CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8082PiperidineHCID 16031Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1)HCID 66854Benzyltrimethylammonium hydroxideHCID 10912012Benzyl 2-Benzylacrylate

Product 1

HCID 19937709Phenylmethyl alpha-[[[2-(diethylamino)ethyl]thio]methyl]benzenepropanoate

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

The oil prepared in Step 10 (1.5 g, 5.95 mmol) is dissolved under argon in methanol (22 mL). To this solution is added 2-diethylaminoethanethiol hydrochloride (1 g, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol) , and the mixture is stirred at room temperature for 16 hours. The solvent is removed on a rotary evaporator and then the residue is purified by flash chromotography on silica gel to give the pure title compound.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. customthe residue is purified by flash chromotography on silica gel

Sources & evidence

ORD record
ord-334a18af66234b7a8a23fa306b8c14f5
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05488066

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes