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

HRID 36376

Reaction equation

HRID 36376 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.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][SH:25].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][S:25][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]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 25798Captamine HydrochlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 10912012Benzyl 2-Benzylacrylate

Product 1

HCID 15296671Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoateYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The title compound of Step 10 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromotography on silica gel, eluting with 20:1 CH2Cl2 :MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was purified by flash chromotography on silica gel
  3. washeluting with 20:1 CH2Cl2

Sources & evidence

ORD record
ord-ec57abf5bbd3413f8d3109fbfd9cb98f
Source dataset
uspto-grants-1995_05
Patent number
US05414018

Linked notes

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