Formamide → HCID 13083337, compound

HRID 325872Notes

Reaction equation

HRID 325872 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:13](=O)[CH3:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:16]([NH2:18])=[O:17]>C(O)=O>[CH:16]([NH:18][CH:13]([CH3:14])[CH2:12][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1)=[O:17]

Participants

4

Reactant 2

HCID 713FormamideHCID 13083375HCID 13083375, compound

Product 1

HCID 13083337HCID 13083337, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
175 °C

Procedure

1-[1-(4-chlorophenyl)cyclobutyl]propan-2-one prepared as described in Example 3 (25 g) and 98% formic acid (10 ml) were added to formamide (22 ml) at 160° C. The temperature was raised to 175° C. and maintained at this temperature for sixteen hours. The mixture was cooled, extracted with dichloromethane. The extract was washed with water and evaporated to give a gum which was crystallised from petroleum ether (b.p. 40°-60° C.) to give N-formyl-2-[1-(4-chlorophenyl)cyclobutyl]-1-methylethylamine (m.p. 71°-73° C.).

Workup

  1. temperaturemaintained at this temperature for sixteen hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. customevaporated
  6. customto give a gum which
  7. customwas crystallised from petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-02f66199090f4d519677b492a41c7156
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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