HCID 22396811, compound → HCID 22396737, compound

HRID 1370372Notes

Reaction equation

HRID 1370372 reaction equation
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]#[C:24][CH2:25][OH:26])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22396811HCID 22396811, compound

Product 1

HCID 22396737HCID 22396737, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(3-benzoyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-10-yl)-2-propyn-1-ol (4.715 g, 13.69 mmol) and 10% Pd/C (0.548 g) in ethanol (75 mL) was hydrogenated under 35 p.s.i. H2 for 3.5 h. The mixture was filtered through celite, rinsed both ethanol, dichloromethane and evaporated. Crystallization from ethyl acetate/hexanes provided 4.230 g of the title compound (mp 144-147° C.). 1H NMR (CDCl3) δ 8.20-8.55, 7.30-7.50, 7.05-7.15, 6.95-7.05, 6.75-6.90, 3.90-4.10, 3.55-3.80, 3.35-3.45, 2.90-3.20, 2.80-2.90, 1.75-2.00.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washrinsed both ethanol, dichloromethane
  3. customevaporated
  4. customCrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5477fb9fc4c54629865b5720af009454
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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