Ammonia → HCID 45789390, compound

HRID 458141Notes

Reaction equation

HRID 458141 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[CH:26](OCC)(OCC)OCC>C(O)(=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([N:17]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH:26]=[N:16][C:14]2=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 31214Ethyl orthoformateHCID 30172231-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carboxamide

Product 1

HCID 45789390HCID 45789390, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 155 g (473 mmol) 1-benzyl-4-(4-fluoro-phenylamino)-piperidine-4-carboxylic acid amide in 200 ml triethyl orthoformate and 100 ml acetic acid was irradiated by microwaves in a sealed reactor to 150° C. for 10 min. and then to 200° C. for further 10 min. The reaction mixture was diluted with water, made alkaline with conc. ammonia, and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was crystallised from Et2O: 85 g 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]dec-2-en-4-one: light brown crystals.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallised from Et2O

Sources & evidence

ORD record
ord-3b5128beb72644b5ab17cff106e2134d
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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