Hydrochloric Acid → Spiro[indene-1,4'-piperidine] hydrochloride

HRID 1590627Notes

Reaction equation

HRID 1590627 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:22]>C(OCC)(=O)C>[ClH:22].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3653579Tert-butyl Spiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1'-(t-Butyloxycarbonyl)spiro(indene-1,4'-piperidine) (16 g, 56 mmole) in ethyl acetate (250 ml) was stirred in an ice bath and saturated with HCl(g) for 30 minutes. The mixture was evaporated to dryness. Ethyl acetate was added and removed in vacuo three times, and the residue was triturated with diethyl ether and filtered to provide spiro(1H-indene-1,4'-piperidine) hydrochloride. The free base was obtained by slurrying the hydrochloride in aqueous sodium bicarbonate solution and extracting with CH2Cl2. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to provide spiro(1H-indene-1,4'piperidine.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionEthyl acetate was added
  3. customremoved in vacuo three times
  4. customthe residue was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-13b8684098b340cf8b77a7bf7d9e8827
Source dataset
uspto-grants-1993_04
Patent number
US05204349

Reaction notes

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