Water → 2,3,4,5-Tetrahydro-5-[(phenylmethoxy)methyl]-1H-pyrido[4,3-b]indol-1-one

HRID 2379138Notes

Reaction equation

HRID 2379138 reaction equation
[C:1]1(=[O:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][NH:2]1.[H-].[Na+].Cl[CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C.C(OCC)(=O)C>[C:21]1([CH2:20][O:19][CH2:18][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[C:1](=[O:14])[NH:2][CH2:3][CH2:4][C:5]2=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 156163232,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 156163242,3,4,5-Tetrahydro-5-[(phenylmethoxy)methyl]-1H-pyrido[4,3-b]indol-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

a solution of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (1.12 g) in dry DMF (60 ml) was treated with sodium hydride (60% dispersion in oil; 480 mg) and the resulting mixture was stirred under nitrogen until effervescence ceased. The mixture was then cooled to 0° and benzyl (chloromethyl) ether (10% w/v solution in DMF; 0,835 ml) was added over 10 min. Stirring was continued for a further 5 min and then water (10 ml) was added. The reaction mixture was concentrated in vacuo to give an oil which was dissolved in ethyl acetate (100 ml) and washed with water (3×100 ml). The organic phase was dried and adsorbed onto FCC silica. Purification by FCC eluting with System A (150:8:1) gave the title compound 1.1 g), m.p. 133°-135°.

Workup

  1. temperatureThe mixture was then cooled to 0°
  2. stirringStirring
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give an oil which
  5. washwashed with water (3×100 ml)
  6. customThe organic phase was dried
  7. customPurification by FCC
  8. washeluting with System A (150:8:1)

Sources & evidence

ORD record
ord-ca25c6bdc7fc4b8dbbbf936d71f345bd
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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