1,2,3,4-Tetrahydroisoquinoline → HCID 14405661, compound

HRID 2166372Notes

Reaction equation

HRID 2166372 reaction equation
C[Al](C)C.[CH2:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][NH:6]1.[C:15]1([CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28](OCC)=[O:29])[CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC.C1(C)C=CC=CC=1>[C:15]1([CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28]([N:6]3[CH2:7][CH2:8][C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH2:5]3)=[O:29])[CH2:24][CH2:23]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 14405661HCID 14405661, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

251 ml (594 mmol) of trimethylaluminium (at a concentration of 25% in hexane) are introduced under an argon atmosphere into 400 ml of toluene. The solution is cooled in an ice bath and 81.5 g (612 mmol) of 1,2,3,4-tetrahydroisoquinoline, dissolved in 200 ml of toluene, are added. The mixture is heated to approximately 50° C. and 95 g (384 mmol) of ethyl 1-phenylmethyl-4-piperidinecarboxylate, dissolved in 400 ml of toluene, are added. The mixture is heated under reflux for 2 h, approximately 250 ml of solvent being removed by means of a Dean and Stark apparatus. The mixture is cooled in an ice bath and hydrolysed by slowly adding 250 ml of water, and the insoluble material is filtered off, it being rinsed with ethyl acetate. The filtrate is washed three times with water, the organic phase dried over sodium sulphate, the solvent evaporated off and the residue recrystallized in cyclohexane. 116.6 g of product are obtained. Melting point: 98°-100° C.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. additionare added
  3. additionare added
  4. temperatureThe mixture is heated
  5. temperatureunder reflux for 2 h
  6. customapproximately 250 ml of solvent being removed by means of a Dean and Stark apparatus
  7. temperatureThe mixture is cooled in an ice bath
  8. additionby slowly adding 250 ml of water
  9. filtrationthe insoluble material is filtered off
  10. washit being rinsed with ethyl acetate
  11. washThe filtrate is washed three times with water
  12. dry with materialthe organic phase dried over sodium sulphate
  13. customthe solvent evaporated off
  14. customthe residue recrystallized in cyclohexane

Sources & evidence

ORD record
ord-6abed2abf00847e7bd3d2b47b5f2fdc7
Source dataset
uspto-grants-1990_07
Patent number
US04945096

Reaction notes

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