Formamide → N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine

HRID 1194446Notes

Reaction equation

HRID 1194446 reaction equation
[C:1]([C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7]1)(=O)[CH2:2][CH2:3][CH3:4].[CH:18]([NH2:20])=[O:19]>C(O)=O>[CH:18]([NH:20][CH:1]([C:6]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH3:4])=[O:19]

Participants

4

Reactant 2

HCID 713FormamideHCID 130833791-Butyryl-1-(3,4-dichlorophenyl)cyclobutane

Product 1

HCID 13083182N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

The ketone produced as described above (37.0 g) and 98% formic acid (9 ml) were added to formamide (23.5 ml) at 170° C. and the temperature kept at 175°-180° C. for five hours. A further portion of formic acid (4.5 ml) was added and the mixture was maintained at 175°-180° C. for a further fifteen hours. The mixture was extracted with ether which on evaporation gave a thick oil which was crystallised from petroleum ether (b.p. 60°-80°) to give N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine having a melting point of 103°-105° C. (Formula I R1 =propyl; R2 =H; R3 =H; R4 =CHO; R5 =4-Cl and R6 =3-Cl).

Workup

  1. temperaturethe mixture was maintained at 175°-180° C. for a further fifteen hours
  2. extractionThe mixture was extracted with ether which on evaporation
  3. customgave a thick oil which
  4. customwas crystallised from petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-6ab1643e875142568665622d6b902f61
Source dataset
uspto-grants-1989_03
Patent number
US04814352

Reaction notes

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