Piperidine → Dibenz[b,f]oxepin-10-yl-piperidin-1-yl-methanone

HRID 1956590Notes

Reaction equation

HRID 1956590 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]1[C:17]2[CH:16]=[C:15]([C:18]([OH:20])=O)[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(CC)CC>CN(C)C=O.ClCCl>[CH:7]1[C:17]2[CH:16]=[C:15]([C:18]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:20])[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 859640Dibenzo[b,f]oxepine-10-carboxylic acid

Product 1

HCID 18663619Dibenz[b,f]oxepin-10-yl-piperidin-1-yl-methanoneYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.1 ml (12.59 mmol) of oxalyl chloride and 1 drop of dimethylformamide are added at room temperature to a solution of 3.0 g is (12.59 mmol) of dibenz[b,f]oxepine-10-carboxylic acid in 20 ml of dichloromethane and the mixture is stirred for 4 hours. 1.86 ml (18.88 mmol) of piperidine and 2.62 ml (18.88 mmol) of Et3N are then added and the mixture is stirred at room temperature overnight. The reaction mixture is washed 1× with hydrochloric acid and brine, and the organic phase is dried, concentrated, subjected to column chromatography and crystallised from tert-butyl methyl ether. 2.64 g (8.6 mmol)=69% of dibenz[b,f]oxepin-10-yl-piperidin-1-yl-methanone are obtained in the form of light-yellow crystals; melting point: 127°-128° C.; 1H-NMR (CDCl3, 200 MHz): 1.30-1.50 (mbr, 2H); 1.50-1.70 (mbr, 4H); 3.30-3.45 (mbr, 2H); 363-3.78 (mbr 2H); 6.92 (s, 1H); 7.10-7.40 (m, 8H); MS: 305 (M+), 221, 193, 165; TLC (silica gel; ethyl acetate/hexane=1:1; UV): Rf =0.32.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. washThe reaction mixture is washed 1× with hydrochloric acid and brine
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customcrystallised from tert-butyl methyl ether

Sources & evidence

ORD record
ord-423a3e8c8f7644cbb1af1e868640aaf9
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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