Acetic Anhydride → HCID 21901895, compound

HRID 722973Notes

Reaction equation

HRID 722973 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[ClH:8].Cl.[NH2:10][C:11]1[CH:12]=[C:13]([C:19](=[O:40])[CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH2:38][CH3:39])[CH2:24][CH2:23]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].C(N(CC)CC)C>O1CCCC1>[ClH:8].[CH2:38]([O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[O:30][CH2:29][CH2:28][N:25]1[CH2:26][CH2:27][CH:22]([CH2:21][CH2:20][C:19]([C:13]2[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([NH:10][C:1](=[O:3])[CH3:2])[CH:12]=2)=[O:40])[CH2:23][CH2:24]1)[CH3:39]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21887766HCID 21887766, compound

Product 1

HCID 21901895HCID 21901895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid anhydride (0.132 ml) was added to a solution of 1-(3-amino-4-methoxyphenyl)-3-{1-[2-(2-ethoxyphenoxy) ethyl]-4-piperidinyl}-1-propanone dihydrochloride (300 mg) obtained in Example 327 and triethylamine (0.195 ml) in tetrahydrofuran (10 ml) at room temperature, the mixture was stirred for 12 hours, and the reaction mixture was concentrated under reduced pressure. Water (30 ml) and ethyl acetate (40 ml) were added to the residue, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1)) to give a free base compound of the title compound as a colorless oil (276 mg), The free base compound (270 mg) was treated with a hydrogen chloride-ethanol solution to give the title compound (277 mg) as colorless crystals having a melting point of 127 to 129° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater (30 ml) and ethyl acetate (40 ml) were added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluting solvent; ethyl acetate-methanol (9:1))

Sources & evidence

ORD record
ord-0b0b07ab02da4e249559844b934af857
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

Loading…