Phenethylamine → trans-1-Benzyl-3-benzylmethylamino-4-hydroxypyrrolidine

HRID 974909Notes

Reaction equation

HRID 974909 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([CH2:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1.O>[CH2:1]([N:8]1[CH2:9][C@@H:10]([OH:11])[C@H:12]([NH:22][CH2:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 69706831trans-1-Benzyl-3-benzylmethylamino-4-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

19.4 g (0.1 mol) of 90% strength 3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane are heated under reflux with 14.5 g (0.12 mol) of benzylmethylamine in 100 ml of dioxane and 200 ml of water overnight. The mixture is extracted with CHCl3, the extracts are dried with K2CO3 and concentrated and the residue is subjected to incipient distillation up to 160° C. (oil bath temperature).

Workup

  1. extractionThe mixture is extracted with CHCl3
  2. dry with materialthe extracts are dried with K2CO3
  3. concentrationconcentrated
  4. distillationdistillation up to 160° C. (oil bath temperature)

Sources & evidence

ORD record
ord-a0a3e4bef1094b96853f1de1984f3d36
Source dataset
uspto-grants-1997_03
Patent number
US05607942

Reaction notes

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