Dichloromethane → HCID 68683499, compound

HRID 1295416Notes

Reaction equation

HRID 1295416 reaction equation
C(O)(=O)C(O)=O.[Br:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][NH:14]2)=[CH:10][CH:9]=1.[OH-].[Na+].C(Cl)[Cl:32]>>[ClH:32].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][NH:14]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68685035HCID 68685035, compound

Product 1

HCID 68683499HCID 68683499, compound

Procedure

1-(4-bromo-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline hydrochloride (33) was prepared as follows: 1-(4-bromo-benzyl)-6,7-dimethoxy -1,2,3,4-tetrahydro-isoquinoline oxalate (1.24 g, 2.74 mmol) was added to a mixture of 50 mL CH2Cl2 and 50 ml of 1N NaOH. The reaction mixture was stirred at room temperature. After dissolving of precipitate, the organic phase was separated, dried over Na2SO4, filtered, and evaporated. A residue was dissolved in MeOH and 10 mL of 1M solution of HCl in Et2O was added. Hydrochloride was crystallized from MeOH—Et2O mixture. Yield is 0.958 g (87.6%).

Workup

  1. dissolutionAfter dissolving of precipitate
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionA residue was dissolved in MeOH
  7. addition10 mL of 1M solution of HCl in Et2O was added
  8. customHydrochloride was crystallized from MeOH—Et2O mixture

Sources & evidence

ORD record
ord-1a82edc9fab34afe8feb88f991b822e5
Source dataset
uspto-grants-2007_07
Patent number
US07241774B2

Reaction notes

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