Propylamine → 1,1-Diphenyl-4-n-propylaminobutane

HRID 258624Notes

Reaction equation

HRID 258624 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH2:21])[CH2:19][CH3:20]>C(O)C>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10][NH:21][CH2:18][CH2:19][CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 768211,1'-(4-Chlorobutylidene)bisbenzene

Product 1

HCID 203209821,1-Diphenyl-4-n-propylaminobutane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 15.0 g. of 1,1-diphenyl-4-chlorobutane and 35 cc. of propylamine in 75 cc. of ethyl alcohol was heated in a sealed bomb at 100° C. for 16 hours. After cooling the reaction mixture to about 25° C., the solvent was removed under reduced pressure. The product was dissolved in 100 cc. of diethyl ether and washed with 5 N sodium hydroxide, and the product was extracted with 2 N hydrochloric acid. The aqueous acidic extracts were combined and the pH was adjusted to 11 by the addition of 5 N sodium hydroxide. The product was insoluble in the aqueous basic solution and was extracted therefrom into diethyl ether. The ethereal extracts were combined, washed with water and dried, and hydrogen chloride gas was added to the ethereal solution. The hydrochloride salt of 1,1-diphenyl-4-n-propylaminobutane crystallized and was collected by filtration. m.p. 94°-96° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe product was dissolved in 100 cc
  3. washof diethyl ether and washed with 5 N sodium hydroxide
  4. extractionthe product was extracted with 2 N hydrochloric acid
  5. additionthe pH was adjusted to 11 by the addition of 5 N sodium hydroxide
  6. extractionwas extracted
  7. washwashed with water
  8. customdried
  9. additionhydrogen chloride gas was added to the ethereal solution
  10. customThe hydrochloride salt of 1,1-diphenyl-4-n-propylaminobutane crystallized
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2a3f4d18a292434e992b4d6c8e2a7a9b
Source dataset
uspto-grants-1977_07
Patent number
US04034011

Reaction notes

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