Potassium Hydroxide → 2,3,4,5-tetrahydro-8-(phenyl-methoxy)-5-(phenylmethyl)-1H-pyrido[4,3-b]indole

HRID 380375Notes

Reaction equation

HRID 380375 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:13]4[CH2:25][CH2:26][N:27](C(OCC)=O)[CH2:28][C:12]=4[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CC(O)C>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:13]4[CH2:25][CH2:26][NH:27][CH2:28][C:12]=4[C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18677421ethyl 1,3,4,5-tetrahydro-8-(phenyl-methoxy)-5-(phenyl-methyl)-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 186774152,3,4,5-tetrahydro-8-(phenyl-methoxy)-5-(phenylmethyl)-1H-pyrido[4,3-b]indoleYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate (2) (0.067 mol) and KOH (0.67 mol) in 2-propanol (250 ml) was stirred and refluxed for 5 hours. The solvent was evaporated. Water (300 ml) was added and the organic solvent was removed azeotropically. The precipitate was filtered off and dissolved in CH2Cl2 (300 ml). The organic solution was dried, filtered and the solvent was evaporated. The residue was washed in CH3CN (50 ml), filtered off and dried, yielding 22.7 g (92%) of 2,3,4,5-tetrahydro-8-(phenyl-methoxy)-5-(phenylmethyl)-1H-pyrido[4,3-b]indole (intermediate 3).

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe solvent was evaporated
  3. additionWater (300 ml) was added
  4. customthe organic solvent was removed azeotropically
  5. filtrationThe precipitate was filtered off
  6. dissolutiondissolved in CH2Cl2 (300 ml)
  7. customThe organic solution was dried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. washThe residue was washed in CH3CN (50 ml)
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-ea7bebb443284143a326c4bdf72fa90e
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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