Pentane → HCID 21486934, compound

HRID 1414285Notes

Reaction equation

HRID 1414285 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:14]([C:27]([NH:29][CH2:30][CH2:31][N:32]([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])=[O:28])[CH2:13][CH2:12]2)C1C=CC=CC=1.CCCCC>CO.[Pd]>[CH:36]([N:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][NH:29][C:27]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=2)[CH:15]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:28])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 8003PentaneHCID 21486938HCID 21486938, compound

Product 1

HCID 21486934HCID 21486934, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.0 Parts of 6-benzyloxy-N-(2-diisopropylamino-ethyl)-7-methoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide is dissolved in approximately 80 parts of methanol. 0.2 Part of a 5% palladium-on-carbon catalyst is added and the mixture is shaken at room temperature and a pressure of about 2 psi for approximately 23 hours or until one molecular equivalent of hydrogen has been absorbed. The catalyst is removed by filtration and the filtrate is concentrated under reduced pressure to give an oil which solidified upon trituration with n-pentane. That solid is crystallized from a mixture of methylene chloride and n-hexane to afford N-(2-diisopropylaminoethyl)-6-hydroxy-7-methoxy-1-phenyl-3,4-dihydro-2(1H)-isoquinolinecarboxamide, melting at about 91°-92°C.

Workup

  1. customuntil one molecular equivalent of hydrogen has been absorbed
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto give an oil which
  5. customThat solid is crystallized from a mixture of methylene chloride and n-hexane

Sources & evidence

ORD record
ord-7778dee7569e4cadbb1d172560a91542
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

Loading…