Benzylamine → N-Benzyl-8-phenyloctan-1-amine

HRID 478087Notes

Reaction equation

HRID 478087 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[NH4+]>CN(C=O)C.O.CCOCC>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 2901511-Chloro-8-phenyloctane

Product 1

HCID 22024865N-Benzyl-8-phenyloctan-1-amineYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 8-phenyloctyl chloride (10.1 g, 44.7 mmol), benzylamine (47.9 g, 44.7 mmol), and anhydrous powdered potassium carbonate in DMF (180 ml) refluxed overnight and cooled to RT. DMF was then evaporated under reduced pressure and water (300 ml) was added to the residue. The oil layer was separated, and the aqueous layer was further extracted with ether (2×150 ml). The ether extracts were evaporated and then combined with the oil layer. The combined oil was diluted with water (250 ml) and acidified with 10% HCl solution to give a white precipitate, 16 g, which was suspended in water (150 ml) and basified with ammonium hydroxide. After being stirred for 10 minutes, most of the white solid went into the solution. Ether (100 ml) was added and stirred for an additional 30 minutes. Organic layer was separated and the aqueous layer was extracted with ether (150 ml×2). Ether extracts were combined, washed with water and saturated brine solution, and dried (MgSO4), thus giving a light yellow oil of 11.90 g (90% yield).

Workup

  1. temperaturerefluxed overnight
  2. customDMF was then evaporated under reduced pressure and water (300 ml)
  3. additionwas added to the residue
  4. customThe oil layer was separated
  5. extractionthe aqueous layer was further extracted with ether (2×150 ml)
  6. customThe ether extracts were evaporated
  7. additionThe combined oil was diluted with water (250 ml)
  8. customto give a white precipitate, 16 g, which
  9. stirringstirred for an additional 30 minutes
  10. customOrganic layer was separated
  11. extractionthe aqueous layer was extracted with ether (150 ml×2)
  12. washwashed with water and saturated brine solution
  13. dry with materialdried (MgSO4)
  14. customthus giving a light yellow oil of 11.90 g (90% yield)

Sources & evidence

ORD record
ord-92b4f34156184f10a80d805a7e885801
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

Loading…