HCID 19777972, compound → HCID 19777992, compound

HRID 2082288Notes

Reaction equation

HRID 2082288 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[O:6][C:7]3[CH:27]=[CH:26][CH:25]=[CH:24][C:8]=3[CH2:9][N:10]([CH2:11][C:12]#[C:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1>[Pd].C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[O:6][C:7]3[CH:27]=[CH:26][CH:25]=[CH:24][C:8]=3[CH2:9][N:10]([CH2:11][CH2:12][CH2:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.[CH:24]1[C:8]2[CH2:9][N:10]([CH2:11][CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=3)[C:4]3[CH:3]=[CH:2][CH:29]=[CH:28][C:5]=3[O:6][C:7]=2[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 19777972HCID 19777972, compound

Product 2

HCID 19777992HCID 19777992, compoundHCID 19777996HCID 19777996, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[3-(8-chloro-10,11-dihydrodibenzo[b,f][1,4]oxazepin-10-yl)prop-1-ynyl]benzoate (2.7 g), 10% palladium-on-charcoal catalyst (0.05 g) and THF (100 ml) was stirred under an atmosphere of hydrogen for 9 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and petroleum ether (b.p. 60°-80° C.) as eluent. There were thus obtained in turn methyl 4-[3-(8-chloro-10,11-dihydrodibenzo[b,f][1,4]oxazepin-10-yl)propyl]benzoate (0.6 g) as a gum and methyl 4-[3-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-10-yl)propyl]benzoate (0.18 g) as a gum.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography
  4. additiona 9:1 v/v mixture of methylene chloride and petroleum ether (b.p. 60°-80° C.) as eluent

Sources & evidence

ORD record
ord-0006344fd30945b6bb5f9acb6cab0043
Source dataset
uspto-grants-1993_02
Patent number
US05189033

Reaction notes

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