Triethylamine → 1-(4,5,7,8-Tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

HRID 611225Notes

Reaction equation

HRID 611225 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[O:2]1[C:6]2[CH2:7][CH2:8][N:9]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 796956-Phenylhexanoic AcidHCID 196002485,6,7,8-Tetrahydro-4H-furo[2,3-d]azepine Hydrochloride

Product 1

HCID 196000531-(4,5,7,8-Tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.138 g of the above crude 5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine hydrochloride, 0.20 g (1.05 mmol) of 6-phenylhexanoic acid and 0.49 ml (3.5 mmol) of triethylamine in 30 ml of dichloromethane, 0.16 ml (1.05 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)

Sources & evidence

ORD record
ord-b30dfc787f234757b3742c694ddb62f3
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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