Acetic Anhydride → HCID 21409851, compound

HRID 1283536Notes

Reaction equation

HRID 1283536 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[CH3:8][NH:9][CH2:10][C:11]1([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)=O>[CH:5]([N:9]([CH2:10][C:11]1([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:8])=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21409890N-Methyl-1-[1-(piperidin-1-yl)cyclohexyl]methanamine

Product 1

HCID 21409851HCID 21409851, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Formic acid 98/100% (13.8 g. 0.3 mole) and acetic anhydride (30.6 g. 0.3 mole) were mixed without cooling and kept at room temp. for 1 hr. 1-(1-methylaminomethylcyclohexyl) piperidine (4.2 g. 0.02 mole) was dissolved in formic acid (15 ml) and the formylating agent (25 ml) added slowly. This produced effervescence and a rise in temp. to 60°. The mixture was allowed to stand at room temp. overnight and the solvents then evaporated under reduced pressure to yield a viscous, amber oil (3.79 g. 80%) which crystallised on cooling and gave colourless prisms of 1-(N-formyl-1-methylaminomethylcyclohexyl) piperidine m.p. 94° (from light petroleum b.p. 60°-80°).

Workup

  1. temperaturewithout cooling
  2. additionthe formylating agent (25 ml) added slowly
  3. customto 60°
  4. waitto stand at room temp. overnight
  5. customthe solvents then evaporated under reduced pressure
  6. customto yield a viscous, amber oil (3.79 g. 80%) which
  7. customcrystallised
  8. temperatureon cooling

Sources & evidence

ORD record
ord-4e1fb03640f8438e9814c2a3df7c9e8f
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

Loading…