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

HRID 36749

Reaction equation

HRID 36749 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]

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 887MethanolSolvent

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-f0be70e54984436190edaae29acd41ab
Source dataset
uspto-grants-1995_05
Patent number
US05416119

Linked notes

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