Acetic Acid → HCID 10735857, compound

HRID 975783Notes

Reaction equation

HRID 975783 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25]OC(OC)OC.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([N:17]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:25]=[N:16][C:14]2=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 10664142HCID 10664142, compound

Product 1

HCID 10735857HCID 10735857, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 1-benzyl-4-(cyclohexylmethylamino)piperidine-4-carboxamide (8 g, 24.32 mmol), 8 ml of trimethoxymethane, 2 ml of acetic acid and 65 ml of toluene was refluxed for 48 hours. The mixture was concentrated. The residue was dissolved in water, made alkaline with aqueous ammonia, and the mixture was extracted with chloroform. The extracts were dried (MgSO4) and concentrated. Recrystallization of the residue from ethyl acetate gave 6.3 g (76.5%) of crystals, mp 117°-118° C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionThe residue was dissolved in water
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-71d9d98cd3cb48b59571de0341bdca82
Source dataset
uspto-grants-1997_03
Patent number
US05610142

Reaction notes

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