HCID 22641362, compound → HCID 135529459, compound

HRID 2415480Notes

Reaction equation

HRID 2415480 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[CH2:24][CH2:25][CH2:26][CH3:27])C1C=CC=CC=1>CO.[Pd]>[CH2:24]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 22641362HCID 22641362, compound

Product 1

HCID 135529459HCID 135529459, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.02 g (2.83 mmol) of the 7-benzyloxy-6-butyl-4-pyrrolidin-1-yl-quinoline, product of example 33, dissolved in 50 ml of MeOH was treated with 0.33 g of palladium on charcoal (10%) and then hydrogenated at RT for 2 h until TLC analysis indicated the completion of the reaction. The catalyst was filtered off, the solution was concentrated in vacuo and the residue was dried in a high vacuum to give 0.65 g (82%) of the 6-butyl-4-pyrrolidin-1-yl-quinolin-7-ol as a light yellow solid. ISP mass spectrum, m/e: 271.3 (M+1 calculated for C17H22N2O: 271).

Workup

  1. customthe completion of the reaction
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution was concentrated in vacuo
  4. customthe residue was dried in a high vacuum

Sources & evidence

ORD record
ord-a12bf4cb6edc4e5b9b29c6b0876e2395
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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