Ethyl orthoformate → HCID 19347344, compound

HRID 1638219Notes

Reaction equation

HRID 1638219 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1([C:22]([NH2:24])=[O:23])[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1.[CH:25](OCC)(OCC)OCC>>[CH2:15]([N:12]1[CH2:11][CH2:10][C:9]2([N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH:25]=[N:24][C:22]2=[O:23])[CH2:14][CH2:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 19347399HCID 19347399, compound

Product 1

HCID 19347344HCID 19347344, compound

Conditions

Temperature
150 °C

Procedure

4-(2-methyl-phenyl-amino)-1-(phenylmethyl)-4-piperidine-carboxamide (10.35 g) was dissolved in 60 ml triethyl orthoformate and stirred at 150° C. for 10 d. After cooling to 0° C, the reaction mixture was evaporated and the resulting brown oil was chromatographed on silica gel using dichloromethane:methanol 19:1 as eluent. 8-benzyl-1-(2-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one (4.71 g) was obtained as a brown foam. MS: m/z=334 (M+H)+

Workup

  1. temperatureAfter cooling to 0° C
  2. customthe reaction mixture was evaporated
  3. customthe resulting brown oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-a63257b673474541a631c2de650b0524
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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