Ethanol → 2-Benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 2393564Notes

Reaction equation

HRID 2393564 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C>C(#N)C.CCOCC>[ClH:1].[CH2:21]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 232984082-Benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline monohydrochloride (2.50 g, 11.6 mmol) and potassium carbonate (2.0 g) in acetonitrile (100 ml) was added benzyl bromide (2.22 g, 13.0 mmol) in acetonitrile (10 ml). The solution was stirred overnight and the solid was then removed by filtration. The solvent was removed in vacuo to give a solid which was partitioned between methylene chloride and water. The dried (MgSO4) organic phase was concentrated and the resulting oil was taken up in ethanol (50 ml). This solution was made acidic with hydrochloric acid in ethanol. The precipitate which formed had set up solid and an additional 150 ml of ethanol and 50 ml of ether was added. The solid was collected and air dried to give 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride as an off white solid (2.78 g (79%)), m.p. 256°-8° C. (dec).

Workup

  1. customthe solid was then removed by filtration
  2. customThe solvent was removed in vacuo
  3. customto give a solid which
  4. customwas partitioned between methylene chloride and water
  5. dry with materialThe dried (MgSO4) organic phase
  6. concentrationwas concentrated
  7. customThe precipitate which formed
  8. customThe solid was collected
  9. customair dried

Sources & evidence

ORD record
ord-22dad46f051044b8b5481c7ca0602f46
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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