Isoquinoline, 3,4-dihydro-1-((3,4-bis(1-methylethoxy)phenyl)methyl)-6,7-diethoxy-, hydrochloride → 1-({3,4-Bis[(propan-2-yl)oxy]phenyl}methyl)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

HRID 325619Notes

Reaction equation

HRID 325619 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[C:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=1)=[N:10][CH2:9][CH2:8]2)[CH3:3].[Na]>CO.C(OCC)C.C(OC(C)C)(C)C>[ClH:1].[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([O:29][CH:30]([CH3:32])[CH3:31])[CH:20]=1)[NH:10][CH2:9][CH2:8]2)[CH3:3]

Participants

6

Reactant 2

HCID 3052865Isoquinoline, 3,4-dihydro-1-((3,4-bis(1-methylethoxy)phenyl)methyl)-6,7-diethoxy-, hydrochlorideHCID 5360545Sodium

Product 1

HCID 30528741-({3,4-Bis[(propan-2-yl)oxy]phenyl}methyl)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)Yield 92.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 7914Diisopropyl EtherSolvent

Procedure

21 g (0.0455 mole) of 6,7-diethoxy-1-(3',4'-diisopropoxybenzyl)-3,4-dihydroisoquinoline hydrochloride was dissolved in 300 ml of methanol in a 1 liter 3-necked flask. The solution was cooled in an ice/water bath and 2.1 g (0.0555 moles) of sodium borhydride was added in two portions with agitation. Stirring was continued for half an hour, the solvent removed under reduced pressure and the residue obtained taken up in 500 ml of diethyl ether. The ethereal solution was washed 3 times with 200 ml of water, dried over sodium sulphate and the solvent removed under reduced pressure. The oil obtained was dissolved in 20 ml of isopropyl ether, and allowed to crystallize. The product was filtered and re-dissolved in 200 ml of diethyl ether, then a solution of hydrochloric acid in diethyl ether added to pH 2. The solvent was removed under reduced pressure and the residue obtained triturated, firstly in isopropyl ether and then in diethyl ether. After drying, 19.5 g of the title hydrochloride was obtained. Yield=92.5%, m.p. 168° C.

Workup

  1. temperatureThe solution was cooled in an ice/water bath
  2. waitwas continued for half an hour
  3. customthe solvent removed under reduced pressure
  4. customthe residue obtained
  5. washThe ethereal solution was washed 3 times with 200 ml of water
  6. dry with materialdried over sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe oil obtained
  9. customto crystallize
  10. filtrationThe product was filtered
  11. dissolutionre-dissolved in 200 ml of diethyl ether
  12. additiona solution of hydrochloric acid in diethyl ether added to pH 2
  13. customThe solvent was removed under reduced pressure
  14. customthe residue obtained
  15. customtriturated, firstly in isopropyl ether
  16. customAfter drying

Sources & evidence

ORD record
ord-4b8a8ccb5d6f4992b4eb5b3b71733f70
Source dataset
uspto-grants-1984_04
Patent number
US04442108

Reaction notes

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