Formic Acid → 4-(N-formylamino)methyl-1-diphenylmethylpiperidine

HRID 362903Notes

Reaction equation

HRID 362903 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[OH-].[Na+].[CH:24](O)=[O:25]>C(OC(=O)C)(=O)C>[CH:24]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:5][CH2:4]1)=[O:25]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 537860464-Aminomethyl-1-diphenylmethylpiperidine

Product 1

HCID 539859804-(N-formylamino)methyl-1-diphenylmethylpiperidineYield 88%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Step 1): To a cooled solution (0°-5° C.) of 4-aminometyl-1-diphenylmethylpiperidine (3.0 g, 0.01 mol) in formic acid (7.5 ml), acetic anhydride (6 ml) was added and the reaction mixture was stirred at room temperature for 17 hours. An aqueous NaOH solution was added to adjust the mixture to pH 12 and the mixture was extracted with ether. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was recrystallized (diisopropyl ether) to give 4-(N-formylamino)methyl-1-diphenylmethylpiperidine (2.9 g, 88%); mp 125° C.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized (diisopropyl ether)

Sources & evidence

ORD record
ord-24dc1f4208e247cda1ccc47aa23ae100
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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