cis-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridine hydrochloride → cis-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridine hydrochloride

HRID 728573Notes

Reaction equation

HRID 728573 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][C@@H:12]2[C:15]3[C:16]([O:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:21][C@@H:11]2[CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[ClH:1].[CH3:23][O:22][C:16]1[C:15]2[C@@H:12]3[C@@H:11]([CH2:10][NH:9][CH2:14][CH2:13]3)[CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 86745061cis-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridine hydrochloride

Product 1

HCID 86745059cis-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridine hydrochlorideYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Example 41 (1.80 g) was combined with 0.90 g 20% Pd/C. in 100 ml methanol and hydrogenated at 4 atm for 4 h. The reaction was filtered and evaporated to yield 1.08 g of the desired product as a white solid, mp: 140-3° C. NMR (d6DMSO) δ 1.70 (m, 1H), 2.02 (m, 1H), 2.60 (m, 1H), 2.78-3.30 (m, 7H), 3.77 (s, 3H), 6.80 (d, 1H), 6.84 (d, 1H), 7.15 (t, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-313cbb7f1b9b4c388557f4f8debb325a
Source dataset
uspto-grants-1991_09
Patent number
US05049564

Reaction notes

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