Dimethylformamide → 6-Phenylazepan-2-one

HRID 569752Notes

Reaction equation

HRID 569752 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN1CCOCC1.CN(C)C=O.Cl.[NH2:31][CH2:32][CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][C:37](O)=[O:38]>C(OCC)(=O)C.O>[C:40]1([CH:33]2[CH2:32][NH:31][C:37](=[O:38])[CH2:36][CH2:35][CH2:34]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 679105716-Amino-5-phenylhexanoic acid hydrochloride

Product 1

HCID 127649286-Phenylazepan-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

27.6 ml of diphenylphosphoryl azide and then 37.5 ml of N-methylmorpholine were added to 260 ml of dimethylformamide containing 26.0 g of 6-amino-5-phenylhexanoic acid hydrochloride [prepared as described in step (c) above] in an ice-bath. The reaction mixture was stirred for 3.5 hours at room temperature, and then dissolved in 0.5 liter of ethyl acetate and 0.5 liter of water. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of ethyl acetate and methylene chloride as eluent, to give 4.0 g of the title compound as crystals, melting at 153.5°-154.5° C. (with decomposition).

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. additionby volume mixture of ethyl acetate and methylene chloride as eluent

Sources & evidence

ORD record
ord-1c7deeb93ff3471b9d9fd5f051853c33
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

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