HCID 22396811, compound → HCID 22396737, compound

HRID 1356244Notes

Reaction equation

HRID 1356244 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-6cc88077e9fc47d483cd8dde8f8f93a0
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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