Hydrogen Bromide → HCID 85822695, compound

HRID 1284193Notes

Reaction equation

HRID 1284193 reaction equation
[CH:1]1([C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(O)[CH2:5][CH2:6][N:7]([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[BrH:17]>>[BrH:17].[Br:17][CH2:3][CH2:2][CH2:1][C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5][CH2:6][N:7]([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 19816208HCID 19816208, compound

Product 1

HCID 85822695HCID 85822695, compound

Procedure

A solution of 30 g. (0.14 mole) of 1-cyclopropyl-3-dimethylamino-1-phenyl-1-propanol in 200 ml. of 48% hydrogen bromide was heated at 100°C. for several minutes and then concentrated on a rotating evaporator. The residual oil was dissolved in isopropanol and treated with ether to give an amorphous solid. Recrystallization of the solid from ethyl acetate gave a nearly pure isomer which after additional recrystallization from isopropylmethyl ketone melted at 128°-130°C. The yield was 2.6 g. (5.2%). The nuclear magnetic resonance spectrum showed the double bond to be in position 2 of the hexenylamine.

Workup

  1. concentrationconcentrated on a rotating evaporator
  2. dissolutionThe residual oil was dissolved in isopropanol
  3. additiontreated with ether
  4. customto give an amorphous solid
  5. customRecrystallization of the solid from ethyl acetate
  6. customgave a nearly pure isomer which
  7. customafter additional recrystallization from isopropylmethyl ketone melted at 128°-130°C

Sources & evidence

ORD record
ord-ac3fb031a21340c3a45d7251c2e7a03f
Source dataset
uspto-grants-1976_08
Patent number
US03978129

Reaction notes

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