Acetic Anhydride → HCID 54043188, compound

HRID 345436Notes

Reaction equation

HRID 345436 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(O)(=O)C>[C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:20][CH:21]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19992424HCID 19992424, compound

Product 1

HCID 54043188HCID 54043188, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-[(4-aminophenoxy)methyl]-1-[4-pyridyl]piperidine (see Preparation 4) (0.57 g), acetic anhydride (1 ml) and acetic acid (1 ml) was heated on a steam bath for 3 hours and then evaporated. The residue was dissolved in water (2 ml) and the solution was made basic with sodium bicarbonate solution. The solid was filtered off, washed with water, dried and then chromatographed on silica gel eluting with dichloromethane/methanol (20:1). Earlier fractions contained impurity and pure product was eluted in the later fractions. The product fractions were combined and evaporated. The solid was crystallised from methanol to give the title compound, (0.34 g), m.p. 226°-228°.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water (2 ml)
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customdried
  6. customchromatographed on silica gel eluting with dichloromethane/methanol (20:1)
  7. washwas eluted in the later fractions
  8. customevaporated
  9. customThe solid was crystallised from methanol

Sources & evidence

ORD record
ord-01cb453ff6c84f8ea9801f592dffd044
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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