Sodium amide → 5,6,7,8-Tetrahydroisoquinolin-1-amine

HRID 1740971Notes

Reaction equation

HRID 1740971 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][N:2]=1.[NH2-:11].[Na+]>C1(C)C(C)=CC=CC=1>[NH2:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 24533Sodium amideHCID 1190105,6,7,8-Tetrahydroisoquinoline

Product 1

HCID 158711865,6,7,8-Tetrahydroisoquinolin-1-amineYield 5.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

Using the method described in Example 63, Step B, a mixture of 2.0 g (15.0 mmol) of 5,6,7,8-tetrahydroisoquinoline and 644 mg (16.5 mmol) of sodium amide in 2.5 mL of xylene was stirred at 150° C. overnight. The crude material was purified by flash column chromatography on silica gel eluting with 0-100% ethyl acetate/dichloromethane, and the partially purified material was distilled using a Kugelrohr apparatus at 100-105° C. (0.3 mm). Recrystallization of the distallate from a hexane/toluene mixture gave 120 mg of 1-amino-5,6,7,8-tetrahydroisoquinoline as a white solid containing approximately 7% of 1-aminoisoquinoline.

Workup

  1. customThe crude material was purified by flash column chromatography on silica gel eluting with 0-100% ethyl acetate/dichloromethane
  2. distillationthe partially purified material was distilled
  3. customat 100-105° C.
  4. customRecrystallization of the distallate from a hexane/toluene mixture

Sources & evidence

ORD record
ord-fa5e87ea1dee45e9838e90f143262a89
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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