Acetic Anhydride → HCID 69497897, compound

HRID 460643Notes

Reaction equation

HRID 460643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C@H:16]([OH:34])[CH2:17][O:18][C:19]3[C:27]4[CH:26]=[C:25]([C:28]5[O:29][C:30]([CH3:33])=[N:31][N:32]=5)[O:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[ClH:1].[C:35]([O:34][C@@H:16]([CH2:15][N:12]1[CH2:11][CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14][CH2:13]1)[CH2:17][O:18][C:19]1[C:27]2[CH:26]=[C:25]([C:28]3[O:29][C:30]([CH3:33])=[N:31][N:32]=3)[O:24][C:23]=2[CH:22]=[CH:21][CH:20]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9806065MIN-117

Product 1

HCID 69497897HCID 69497897, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-1-(4-(3,4-Dichlorophenyl)piperidino)-3-(2-(5-methyl-1,3,4-oxadiazol-2-yl)benzo(b)furan-4-yloxy)-2-propanol (1.0 g) was dissolved in pyridine (20 ml) and acetic anhydride (10 ml), and the mixture was left standing at room temperature for 12 hr. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol). The obtained oil was dissolved in ethanol and a solution of hydrogen chloride in ether was added. The precipitated crystals were collected by filtration and dried to give the title compound (0.58 g) as pale-yellow crystals, melting point 163–166° C. (decomposition)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol)
  3. dissolutionThe obtained oil was dissolved in ethanol
  4. additiona solution of hydrogen chloride in ether was added
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-bc1aa9e658ef4ceb8ac4c23e21ab2830
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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