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

HRID 2210294Notes

Reaction equation

HRID 2210294 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:22]C(Cl)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)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 63651,1-DichloroethaneHCID 46872381'-(Phenylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine]

Product 1

HCID 225093272,3-Dihydrospiro[indene-1,4'-piperidine] hydrochloride

Conditions

Temperature
0 °C

Procedure

1'-Benzyl-2,3-dihydrospiro[1H-indene-l,4'-piperidine](0.50 g, 1.80 mmol) was dissolved in dichloroethane (6 mL). The resulting solution was cooled to 0° C. and 1-chloro-ethylchloroformate (0.258 g, 1.80 mmol) was added in one batch. Cooling was continued for 10 min after which the reaction mixture was refluxed for 1 h, cooled to room temperature and concentrated under reduced pressure. The residue was redissolved in MeOH (10 mL) and refluxed for 2 h. The resulting solution was concentrated under reduced pressure to obtain (0.40 g, quant.) of a pale yellow crystalline solid; m.p. 256°-257° C. (lit. 288-290); 1H NMR (CDCl3):δ1.74 (br d, 2, piperidyl β-Heq), 2.10 (td, 2, piperidyl β-Hax), 2.13 (t, 2, Ph-CH2 --CH2--, J= 6 Hz), 2.94 (t, 2, J=6 Hz, Ph-CH2 --), 3.12-3.38 (m, 4, piperidyl αHax,eq), d=7.19 (br s, 4, phenyl). MS (EI) m/e 187.2 (M+ of free base).

Workup

  1. temperatureCooling
  2. temperatureafter which the reaction mixture was refluxed for 1 h
  3. temperaturecooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was redissolved in MeOH (10 mL)
  6. temperaturerefluxed for 2 h
  7. concentrationThe resulting solution was concentrated under reduced pressure
  8. customto obtain (0.40 g, quant.) of a pale yellow crystalline solid

Sources & evidence

ORD record
ord-bb5031bd8d2d43708b2c93a95e130d29
Source dataset
uspto-grants-1995_10
Patent number
US05457207

Reaction notes

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