Formamide → HCID 18007168, compound

HRID 2299646Notes

Reaction equation

HRID 2299646 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][C:9]=2[CH:23]=1)=O.C[O-].[Na+].O.C([NH2:30])=O>>[CH2:16]([NH:15][CH:11]1[CH2:10][C:9]2[CH:23]=[C:5]([C:3]([NH2:30])=[O:2])[CH:6]=[CH:7][C:8]=2[CH2:14][CH2:13][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 10942334Sodium MethoxideHCID 54157148HCID 54157148, compound

Product 1

HCID 18007168HCID 18007168, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid methyl ester (4.21 g) and sodium methoxide (2.21 g) in formamide (42 ml) was heated at 110° C. for 2 hours. After cooling, the reaction mixture was poured into water, and the product was extracted with ethyl acetate. The organic layer was washed with water (twice) and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1 to 10:1) to afford 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxamide (2.71 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water (twice) and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1 to 10:1)

Sources & evidence

ORD record
ord-2da0a4ccdef548afae668c6353688259
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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