Spiro[indene-1,4'-piperidine] hydrochloride → 2,3-Dihydrospiro[indene-1,4'-piperidine] hydrochloride

HRID 1110039Notes

Reaction equation

HRID 1110039 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:4][CH2:3]1>C(O)C.[Pd]>[ClH:1].[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 22509344Spiro[indene-1,4'-piperidine] hydrochloride

Product 1

HCID 225093272,3-Dihydrospiro[indene-1,4'-piperidine] hydrochlorideYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of spiro[indene-1,4'-piperidine]hydrochloride (1.9 g, 8.6 mmol) in ethanol (50 ml) was hydrogenated at 50 p.s.i. for 1 hour, in the presence of 10% palladium on carbon (0.3 g, 16% (w/w)). The catalyst was filtered off, and the ethanol removed in vacuo. The remaining solid was recrystallised from 4:1 ethyl acetate:ethanol to give spiro[indane-1,4'-piperidine]hydrochloride (814 mg, 43%) as a white crystalline solid. N.M.R. (D2O) δ 1.79 (2H, d, J=14 Hz), 2.06 (2H, t of d, J=14 and 4 Hz), 2.14 (2H, t, J=7 Hz), 2.98 (2H, t, J=7 Hz), 3.25 (2H, t of d, J=14 and 2 Hz), 3.48 (2H, m), 7.33 (4H, m)

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe ethanol removed in vacuo
  3. customThe remaining solid was recrystallised from 4:1 ethyl acetate

Sources & evidence

ORD record
ord-7e05cd682b4645f4b44970ecaa8af71a
Source dataset
uspto-grants-1994_06
Patent number
US05324733

Reaction notes

Loading…