Hydrochloric Acid → HCID 59323338, compound

HRID 2390029Notes

Reaction equation

HRID 2390029 reaction equation
[NH:1]([CH2:8][C:9]([N:11]1[CH:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[C:2]1([NH:1][CH2:8][CH2:9][N:11]2[CH:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59323248HCID 59323248, compound

Product 1

HCID 59323338HCID 59323338, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 mg of 2-(2-anilinoacetyl)-3-benzyl-1,2,3,4-tetrahydroisoquinoline was dissolved in 1 mL of THF, and 1.1 mg of LAH was added thereto under an argon atmosphere, followed by stirring under ice-cooling 2 hours. After completion of the reaction, 2N hydrochloric acid was added thereto, and when foaming was stopped, a saturated aqueous sodium bicarbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation, followed by purification using PLC (chloroform:methanol=10:1) to obtain 2.5 mg (yield 26%) of a title compound as a pale yellow oily substance.

Workup

  1. temperaturecooling 2 hours
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation
  7. customfollowed by purification

Sources & evidence

ORD record
ord-fe695544495e410e9d3575747af74205
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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