HCID 19372685, compound → HCID 19372675, compound

HRID 129093Notes

Reaction equation

HRID 129093 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH2:25]O)=[O:22])=[CH:17][C:16]=3[F:27])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1>O1CCCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:22][CH2:25][CH2:24][N:23]=4)=[CH:17][C:16]=3[F:27])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 19372685HCID 19372685, compound

Product 1

HCID 19372675HCID 19372675, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.4 g (0.95 mmol) of 1-(4-chlorobenzoyl)-4-[2-fluoro-4-(2-hydroxyethylaminocarbonyl)benzylidene]piperidine in 20 ml of tetrahydrofuran are treated with 0.3 g (1.1 mmol) of methyl N-(triethylamoniosulphonyl)carbamate (Burgess reagent) in portions, at boiling temperature, during the course of 45 minutes. The mixture is heated for a further 2 hours and evaporated down, and the residue is mixed with water, the mixture is extracted three times with methylene chloride, the extract is dried with anhydrous sodium sulphate and evaporated down, and the residue is purified on a Silica gel column (ethyl acetate/petroleum ether=10:4, v/v). 0.105 g (26% of theory) of the title compound of melting point 158°-160° C. is obtained.

Workup

  1. customduring the course of 45 minutes
  2. temperatureThe mixture is heated for a further 2 hours
  3. customevaporated down
  4. additionthe residue is mixed with water
  5. extractionthe mixture is extracted three times with methylene chloride
  6. dry with materialthe extract is dried with anhydrous sodium sulphate
  7. customevaporated down
  8. customthe residue is purified on a Silica gel column (ethyl acetate/petroleum ether=10:4, v/v)

Sources & evidence

ORD record
ord-587fa05b4fe3406bb6ddd6ac8e9c021d
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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