Phosphorus oxychloride → 6,7-Bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1295411Notes

Reaction equation

HRID 1295411 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:15]([O:27][CH2:28]C3C=CC=CC=3)[CH:14]=2)=O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:43])=O.[BH4-].[Na+]>C(#N)C.Cl>[ClH:43].[CH2:28]([O:27][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][C:16]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:2][CH:3]=1)[NH:10][CH2:11][CH2:12]2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 117858292-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide

Product 1

HCID 160865076,7-Bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

6,7-bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride (2) was prepared as follows: A stirred solution of 3 g (5.69 mmol) of 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide and 5.6 ml (60 mmol) of phosphorus oxychloride in 25 ml of anhydrous acetonitrile was refluxed for 20 hours. The reaction solution was evaporated under reduced pressure and the residue was dissolved in 25 ml of methanol. To this stirred solution at 0° C., 2.27 g (60 mmol) of sodium borohydride was added portionwise. The stirred reaction mixture was allowed to reach room temperature overnight and then it was poured in 150 ml of 10% aqueous HCl solution. The precipitate was collected on a glass filter funnel, washed with water (3×50 ml), and air-dried overnight. The solid was recrystallized using ether/methanol mixture to provide 2.56 g (82%) of off-white crystals, mp 187-189° C.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 25 ml of methanol
  3. customThe stirred reaction mixture
  4. customThe precipitate was collected on a glass
  5. filtrationfilter funnel
  6. washwashed with water (3×50 ml)
  7. customair-dried overnight
  8. customThe solid was recrystallized

Sources & evidence

ORD record
ord-c2facd33e9a344f89bb695b2f092ee32
Source dataset
uspto-grants-2007_07
Patent number
US07241774B2

Reaction notes

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