Formic Acid → HCID 23284946, compound

HRID 369173Notes

Reaction equation

HRID 369173 reaction equation
C(O)=O.[C:4]1([CH2:10][CH2:11][NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:26]=O.[ClH:28]>C(O)C>[ClH:28].[ClH:28].[CH3:26][N:12]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14]1)[CH2:11][CH2:10][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1378357HCID 1378357, compound

Product 1

HCID 23284946HCID 23284946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

136 ml of formic acid was added to 210 g of 4-(2-phenylethylamino)-1-benzylpiperidine. Since the temperature of the mixture increased to about 90° C., the mixture was ice-cooled. To the reaction mixture was added 64 ml of 37% formalin at 50-60° C.; the ice bath was removed; and the mixture was stirred for 1 hour. To the resulting reaction mixture were added 1 liter of ethanol and 120 ml of concentrated hydrochloric acid, followed by concentration under reduced pressure. To the residue was added 1 liter of ethanol. The resulting insolubles were collected by filtration and then washed with ethanol to obtain 251.7 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-benzylpiperidine dihydrochloride as a white powder.

Workup

  1. temperaturecooled
  2. customthe ice bath was removed
  3. customTo the resulting reaction mixture
  4. concentrationfollowed by concentration under reduced pressure
  5. additionTo the residue was added 1 liter of ethanol
  6. filtrationThe resulting insolubles were collected by filtration
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-971c1dad428d43bfba33abdc7f27bf63
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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