Thiophene → 2,3,4,5-tetrahydro-2-[1-(phenylmethyl)-4-piperidinyl]-1H-pyrido[4,3-b]indole

HRID 380380Notes

Reaction equation

HRID 380380 reaction equation
[CH2:1]1[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.[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([N:2]3[CH2:3][CH2:4][C:5]4[NH:6][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=5[C:13]=4[CH2:1]3)[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 192201-Benzyl-4-piperidoneHCID 7232301H,2H,3H,4H,5H-pyrido[4,3-b]indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 186774092,3,4,5-tetrahydro-2-[1-(phenylmethyl)-4-piperidinyl]-1H-pyrido[4,3-b]indoleYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indole (0.2 mol) and 1-(phenyl-methyl)-4-piperidinone (0.2 mol) in methanol (700 ml) was hydrogenated at 50° C. with palladium-on-charcoal (10%; 3 g) as a catalyst in the presence of thiophene (4%; 2 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 69 g 2,3,4,5-tetrahydro-2-[1-(phenylmethyl)-4-piperidinyl]-1H-pyrido [4,3-b]indole (intermediate 24).

Workup

  1. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-69fffccc6aaa46758a2689f9d55ec79b
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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