Water → HCID 19806404, compound

HRID 1681356Notes

Reaction equation

HRID 1681356 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1.O>CO>[C:10]1([CH:8]([OH:9])[CH:7]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 185583(R,R)-Stilbene oxideHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 19806404HCID 19806404, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mol) and 4-amino-1-benzylpiperidine (5.70 g, 0.030 mol) was heated at 145° C. in an oil bath for 15 hours. The cooled mixture was then dissolved in methanol (20 mL) and the solution poured into water (200 mL). The product separated as an oil that solidified on standing. The solid was collected and dried under ambient conditions for 18 hours to obtain 3.68 g (95%) of material. Recrystallization from toluene-isooctane gave 2.31 g of the product as a tan solid; mp 128°-130° C.

Workup

  1. customThe product separated as an oil that
  2. customThe solid was collected
  3. customdried under ambient conditions for 18 hours

Sources & evidence

ORD record
ord-52c523da79e14c638931393d684d0e68
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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