Water → HCID 18677421, compound

HRID 1634181

Reaction equation

HRID 1634181 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[NH:14][C:13]4[CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:13]4[CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][C:12]=4[C:11]=3[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18677416ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 18677421HCID 18677421, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of intermediate (1) (0.09 mol) in N,N-dimethylformamide (200 ml) was stirred at 10° C. under a N2 flow. Sodium hydride (60%; 0.1 mol) was added portionwise. The mixture was stirred for 1 hour at room temperature, then it was cooled to 5° C. Benzylbromide (0.1 mol) was added dropwise. Stirring was continued for 2 hours. The mixture was cooled to 10° C. and poured out into cold water (500 ml). This mixture was extracted with CH2Cl2 (2×250 ml). The separated organic layer was washed with water (100 ml), dried, filtered and the solvent was evaporated. The solid residue was washed with CH3CN (50 ml), cooled and the resulting precipitate was filtered off and dried, yielding 30.0 g (76%) of ethyl 1,3,4,5-tetrahydro-8-(phenylmethoxy)-5-(phenyl-methyl)-2H-pyrido[4,3-b]indole-2-carboxylate (intermediate 2).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. temperatureit was cooled to 5° C
  3. stirringStirring
  4. temperatureThe mixture was cooled to 10° C.
  5. extractionThis mixture was extracted with CH2Cl2 (2×250 ml)
  6. washThe separated organic layer was washed with water (100 ml)
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. washThe solid residue was washed with CH3CN (50 ml)
  11. temperaturecooled
  12. filtrationthe resulting precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-4ff73a8b896a4053847000814face05c
Source dataset
uspto-grants-2003_01
Patent number
US06506768B2

Linked notes

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