HCID 13166247, compound → HCID 19862668, compound

HRID 1165277Notes

Reaction equation

HRID 1165277 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][O:13][CH3:14])[CH:6]=1)=[O:4].Br.[C:16]1([CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([CH2:2][N:32]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:4])=[CH:6][C:7]=1[CH2:12][O:13][CH3:14]

Participants

4

Reactant 2

HCID 13166247HCID 13166247, compoundHCID 19798064N-Benzyl-6-(3-phenylpropoxy)hexan-1-amine--hydrogen bromide (1/1)

Product 1

HCID 19862668HCID 19862668, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-1-[4-hydroxy-3-(methoxymethyl)phenyl]ethanone (700 mg), N-[6-(3-phenylpropoxy)hexyl]benzenemethanamine hydrobromide (1.1 g) and DEA (0.95 ml) in dichloromethane (10 ml) was kept at room temperature overnight. ER (50 ml) was added and the suspension was washed twice with water, brine, dried and concentrated to an oil which was dissolved in ethanol (20 ml) and treated with sodium (400 mg). The solution was stirred and refluxed refluxed overnight, water (30 ml) was added and the mixture was extracted with ER (3×25 ml). The organic extracts were washed with brine, dried and concentrated to a red oil which was purified by FCC eluting with System E (80:20:1→66:33:1) to give the title compound as an oil (250 mg), t.l.c. (System E 66:37:1) Rf 0.22.

Workup

  1. additionER (50 ml) was added
  2. washthe suspension was washed twice with water, brine
  3. customdried
  4. concentrationconcentrated to an oil which
  5. dissolutionwas dissolved in ethanol (20 ml)
  6. additiontreated with sodium (400 mg)
  7. temperaturerefluxed
  8. temperaturerefluxed overnight
  9. additionwater (30 ml) was added
  10. extractionthe mixture was extracted with ER (3×25 ml)
  11. washThe organic extracts were washed with brine
  12. customdried
  13. concentrationconcentrated to a red oil which
  14. customwas purified by FCC
  15. washeluting with System E (80:20:1→66:33:1)

Sources & evidence

ORD record
ord-0142d6016e3d4b348109b348c4517fa6
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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