Acetic Anhydride → HCID 60078094, compound

HRID 2085211Notes

Reaction equation

HRID 2085211 reaction equation
[OH:1][C@@H:2]([CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>N1C=CC=CC=1>[C:37]([O:1][C@@H:2]([CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9913387HCID 9913387, compound

Product 1

HCID 60078094HCID 60078094, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-4-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)-N-methoxy-N-methylbenzo(b)furan-2-carboxamide (0.40 g) obtained in Example 6 was dissolved in pyridine (20 ml) and acetic anhydride (10 ml) was added at room temperature. The mixture was stood for one day. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give (S)-4-(2-acetoxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)-N-methoxy-N-methylbenzo(b)furan-2-carboxamide (0.34 g) as a brown oil. This was dissolved in ethanol and maleic acid (0.10 g) was added. The precipitated crystals were collected by filtration and dried to give the title compound (0.25 g) as pale-yellow crystals, melting point 125-127° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-b3d782e29b944a01ab5135910f7966c4
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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