HCID 69289921, compound → HCID 136360253, compound

HRID 2415481Notes

Reaction equation

HRID 2415481 reaction equation
[ClH:1].[N:2]1([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19]CC4C=CC=CC=4)=[CH:16][CH:17]=3)[N:12]=[C:11]([CH3:27])[CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>CO.[Pd]>[ClH:1].[N:2]1([C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[N:12]=[C:11]([CH3:27])[CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 69289921HCID 69289921, compound2×

Product 1

HCID 136360253HCID 136360253, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.45 g (3.78 mmol) of 4-azepan-1-yl-7-benzyloxy-2-methyl-quinoline hydrochloride, product of example 39, dissolved in 120 ml of MeOH was treated with 700 mg of palladium on charcoal (10%) and then hydrogenated at RT for 2 h until HPLC analysis indicated the completion of the reaction. The catalyst was filtered off, washed with water, and the solution was concentrated in vacuo. The residue was triturated with diethyl ether, the solid obtained was filtered off by suction and dried in a high vacuum to give 1 g (90.4%) 4-azepan-1-yl-2-methyl-quinolin-7-ol hydrochloride as a light gray solid. ISP mass spectrum, m/e: 257.2 (M+1 calculated for C16H20N2O: 257).

Workup

  1. customthe completion of the reaction
  2. filtrationThe catalyst was filtered off
  3. washwashed with water
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was triturated with diethyl ether
  6. customthe solid obtained
  7. filtrationwas filtered off by suction
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-acd0b55213e84430a651901648396de6
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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