Benzyl Bromide → Acetyl 9-benzyl-1,2,3,4-tetrahydro-beta-carboline

HRID 1681152Notes

Reaction equation

HRID 1681152 reaction equation
[C:1]([CH:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][NH:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[C:1]([CH:4]1[C:16]2[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][NH:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19807225Acetyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 54345929Acetyl 9-benzyl-1,2,3,4-tetrahydro-beta-carboline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 acetyl-9 benzyl-1,2,3,4-tetrahydro-β-carboline was prepared as follows: Under a nitrogen atmosphere, 8.0 mmol of 2 acetyl-1,2,3,4-tetrahydro-β-carboline (1.71 was dissolved in 4Q mL dry dimethylformamide (DMF). The solution was stirred over ice, and NaH (2 g) was added under N2. The suspension was stirred for 1 hour, and then benzylbromide (9.2 mmol, 1.56 was slowly to the cooled suspension. After a further 2 hours of stirring at ambient temperature, the mixture was filtered and the filtrate added to 320 mL 0.1 N HCl. Crude 2-acetyl- 9-benzyl-1,2,3,4-tetrahydro-β-carboline separated as an oil. The oil was collected by centrifugation, washed with water, and dried over anhydrous MgSO:. The product was purified by standard chromatographic procedures using a 60:40 mixture of ether:hexane.

Workup

  1. additionwas added under N2
  2. stirringAfter a further 2 hours of stirring at ambient temperature
  3. filtrationthe mixture was filtered
  4. additionthe filtrate added to 320 mL 0.1 N HCl
  5. customCrude 2-acetyl- 9-benzyl-1,2,3,4-tetrahydro-β-carboline separated as an oil
  6. customThe oil was collected by centrifugation
  7. washwashed with water
  8. dry with materialdried over anhydrous MgSO
  9. customThe product was purified by standard chromatographic procedures
  10. additiona 60:40 mixture of ether

Sources & evidence

ORD record
ord-f3d60b7a64564e9d91b2ea65bf6dcd9d
Source dataset
uspto-grants-1992_12
Patent number
US05169852

Reaction notes

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