Sodium Hydroxide → HCID 131718542, compound

HRID 1728654Notes

Reaction equation

HRID 1728654 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH:7]([CH2:20][OH:21])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH2:22]1[O:26][C:25]2[CH:27]=[C:28](O)[CH:29]=[CH:30][C:24]=2[O:23]1.[OH-].[Na+].[ClH:34].CN1CC[C@@H](C2C=CC([N+]([O-])=O)=CC=2)[C@H](COC2C=CC3OCOC=3C=2)C1>CC(CC(O)C)C>[ClH:34].[CH2:1]([N:5]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH3:18])[CH3:19])=[CH:15][CH:16]=2)[C@H:7]([CH2:20][O:21][C:28]2[CH:29]=[CH:30][C:24]3[O:23][CH2:22][O:26][C:25]=3[CH:27]=2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 68289SesamolHCID 19014393HCID 19014393, compoundHCID 131718535HCID 131718535, compound

Product 1

HCID 131718542HCID 131718542, compound

Reagents, catalysts & solvents 1

HCID 79104-Methyl-2-PentanolSolvent

Procedure

3-benzenesulphonyloxymethyl-1-butyl-4-(4-dimethyl-aminophenyl)piperidine (16) (2 g) (prepared from compound (12), benzenesulphonyl chloride and triethylamine by known procedures) was treated with sesamol (0.73 g) and NaOH (0.21 g) in MIBC as described for the preparation of compound (1). Reflux for 2 h. The crude product was purified several times on a silica gel column using CH2Cl2 /CH3OH 9/1 as eluent. Yield 0.05 g of colorless crystals after precipitation as the hydrochloride. M.p. 211.5°-214° C.

Workup

  1. temperatureReflux for 2 h
  2. customThe crude product was purified several times on a silica gel column
  3. customYield 0.05 g of colorless crystals after precipitation as the hydrochloride

Sources & evidence

ORD record
ord-32bf5b6cc4b04858a090265110e015a7
Source dataset
uspto-grants-1994_07
Patent number
US05328917

Reaction notes

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