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

HRID 345810Notes

Reaction equation

HRID 345810 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-729b3693579d4d7ab8a8e1cb0324df61
Source dataset
uspto-grants-1991_10
Patent number
US05059597

Reaction notes

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