Water → 1-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl](phenylmethyl)amino]ethanone

HRID 1088720Notes

Reaction equation

HRID 1088720 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=1)=[O:4].[C:14]1([CH2:20][O:21][C:22]2[C:23]([CH2:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.CCOCC>C1COCC1>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:38]([CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][CH2:28][C:23]2[C:22]([O:21][CH2:20][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:6][C:7]=1[CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneHCID 54019079N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine

Product 1

HCID 221617531-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl](phenylmethyl)amino]ethanoneYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (460 mg), N-[6-[3-[3-(phenylmethoxy)-2-pyridinyl]propoxy]hexyl]benzenemethanamine (800 mg) and DEA (485 mg) in THF (15 ml) was left at room temperature overnight. Water (30 ml) and ether (30 ml) were added, the phases were separated and the organic layer was re-extracted with ether (50 ml). The combined extracts were washed with water and brine, dried and concentrated to an oil which was purified by FCC eluting with ethyl acetate/triethylamine (99:1) followed by ethyl acetate/methanol/triethylamine (90:10:1) to give the title compound as an orange oil (620 mg), t.l.c. (ethyl acetate/methanol/triethylamine 80:20:1) Rf 0.66.

Workup

  1. customthe phases were separated
  2. extractionthe organic layer was re-extracted with ether (50 ml)
  3. washThe combined extracts were washed with water and brine
  4. customdried
  5. concentrationconcentrated to an oil which
  6. customwas purified by FCC
  7. washeluting with ethyl acetate/triethylamine (99:1)

Sources & evidence

ORD record
ord-1a0a2b06a7af47bd8738b09c5944e96a
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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