Acetic Anhydride → N-[[1-(4-Methyl-1-piperazinyl)cyclohexyl]methyl]formamide

HRID 1283538Notes

Reaction equation

HRID 1283538 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[NH2:8][CH2:9][C:10]1([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)=O>[CH:5]([NH:8][CH2:9][C:10]1([N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70181321-[1-(4-METHYLPIPERAZIN-1-YL)CYCLOHEXYL]METHANAMINE

Product 1

HCID 21409858N-[[1-(4-Methyl-1-piperazinyl)cyclohexyl]methyl]formamideYield 66.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Formic acid (6.9 g, 0.15 mole) and acetic anhydride (15.3 g, 0.15 mole) were mixed without cooling and kept at room temperature for 1 hr. 1-(1-aminomethylcyclohexyl)-4-methylpiperazine (8.4 g, 0.04 mole) was dissolved in formic acid (12 ml) and the formylating mixture (16 ml) added. This produced vigorous effervescence and a rise in temperature to 70°. The mixture was left at room temperature for 2 hr. and then heated on a water bath at 55° for 0.75 hr. The solvents were removed under reduced pressure yielding a viscous brown oil (6.0 g, 66.3%) which crystallised as colourless plates of 1-(1-formylaminomethylcyclohexyl)-4-methylpiperazine from light petroleum (b.p. 80°-100°), m.p. 97°-98°.

Workup

  1. temperaturewithout cooling
  2. customto 70°
  3. waitThe mixture was left at room temperature for 2 hr
  4. temperatureand then heated on a water bath at 55° for 0.75 hr
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-241ea3775672480f85f02010d4ef4aca
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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