Benzaldehyde → HCID 59323388, compound

HRID 2390026Notes

Reaction equation

HRID 2390026 reaction equation
[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][N:9]1[CH2:18][CH2:19][NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:21]([NH:20][CH2:19][CH2:18][N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59323222HCID 59323222, compound

Product 1

HCID 59323388HCID 59323388, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

26 mg of 2-[3-benzyl-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine was dissolved in 1 mL of toluene, and MS-4A (30 mg), 10.4 mg of benzaldehyde, 18 mg of sodium triacetoxyborohydride, and 0.01 mL of acetic acid were added thereto at room temperature, followed by stirring overnight. After completion of the reaction, to the reaction liquid was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified using PLC (chloroform:methanol=20:1) to obtain 24.4 mg (yield 70%) of a title compound as a pale yellow oily substance.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customto the reaction liquid
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified

Sources & evidence

ORD record
ord-16e4fe80bd994ca08df94113e330d922
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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