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

HRID 36677Notes

Reaction equation

HRID 36677 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-e4610c5c74bb4545a47295a6bea3bdfd
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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