1-Bromo-3-chloropropane → HCID 20079736, compound

HRID 1464144Notes

Reaction equation

HRID 1464144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][NH:18][CH3:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][Cl:30]>CN(C)C=O>[Cl:30][CH2:29][CH2:28][CH2:27][N:18]([CH3:19])[CH2:17][C:11]1([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 20079735HCID 20079735, compound

Product 1

HCID 20079736HCID 20079736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.40 g (0.0129 mol) of 1-(3,4-dimethoxyphenyl)-N-methyl-1-cyclohexanemethanamine in 50 ml of abs. dimethylformamide was treated with 3.57 g (0.0258 mol) of anhydrous potassium carbonate. The mixture was stirred at 5° and treated with 1.4 ml (0.0129 mol) of 1-bromo-3-chloropropane and subsequently stirred initially at 30° for 4 hours and thereafter at room temperature for 16 hours. The solvent was then evaporated at room temperature under reduced pressure and the residue was treated with water. The mixture was extracted three times with ether and the organic extracts were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oily residue was distilled under a pressure of 300 Pa at 195°, whereby there was obtained N-(3-chloropropyl)-1-(3,4-dimethoxyphenyl)-N-methylcyclohexanemethanamine as a colourless viscous oil which was used directly in the next step.

Workup

  1. stirringsubsequently stirred initially at 30° for 4 hours
  2. customThe solvent was then evaporated at room temperature under reduced pressure
  3. additionthe residue was treated with water
  4. extractionThe mixture was extracted three times with ether
  5. dry with materialthe organic extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. distillationThe oily residue was distilled under a pressure of 300 Pa at 195°

Sources & evidence

ORD record
ord-e9fb16df01d04d7b9d45f8dc4f3c31b1
Source dataset
uspto-grants-1994_04
Patent number
US05302727

Reaction notes

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