Bromocyclopentane → HCID 20299743, compound

HRID 1733496Notes

Reaction equation

HRID 1733496 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1>O>[CH:21]1([N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium Carbonate2×HCID 10488031HCID 10488031, compound

Product 1

HCID 20299743HCID 20299743, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 3.4 g of 3-methoxy-N-propyl-benzeneethanamine, 4 g of potassium carbonate and 15 ml of cyclopentyl bromide was refluxed for one hour after which 5 g of potassium carbonate were added thereto and the mixture was refluxed for another 3 hours. The mixture was poured into 50 ml of water and the mixture was extracted 3 times with 50 ml of ether. The organic phase was dried and filtered and the filtrate was evaporated to dryness to obtain 4.5 g of N-cyclopentyl-3-methoxy-N-propylbenzeneethanamine in the form of a red oil which was used as is for the next step.

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for another 3 hours
  3. extractionthe mixture was extracted 3 times with 50 ml of ether
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-5fc2c2384a084d33a484c674646d85ce
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

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