1-Chloroethyl chloroformate → 6-Chlorospiro[chroman-2,4'-piperidine] hydrochloride

HRID 270047Notes

Reaction equation

HRID 270047 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:23])[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C1(C)C=CC=CC=1>[ClH:23].[Cl:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[O:14][C:11]1([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH2:22][CH2:21]2

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 598336421'-Benzyl-6-chloro-3,4-dihydrospiro[chromene-2,4'-piperidine]

Product 1

HCID 689620726-Chlorospiro[chroman-2,4'-piperidine] hydrochlorideYield 84.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1′-benzyl-6-chloro-3,4-dihydrospiro[chromene-2,4′-piperidine] (1.63 g, 5.0 mmol) and 1-chloroethyl chloroformate (1.07 g, 7.5 mmol) in toluene (5 ml) was heated with reflux overnight. The solvent was removed i. vacuo, the oily residue dissolved in methanol (10 ml) and heated with reflux overnight. The solvent was removed in vacuo, and the residue treated with diethyl ether (50 ml). The white precipitate was collected by filtration, washed with diethyl ether and dried to afford the subtitle compound as white powder (0.58 g, 49%).

Workup

  1. temperaturewith reflux overnight
  2. customThe solvent was removed i
  3. dissolutionvacuo, the oily residue dissolved in methanol (10 ml)
  4. temperatureheated
  5. temperaturewith reflux overnight
  6. customThe solvent was removed in vacuo
  7. additionthe residue treated with diethyl ether (50 ml)
  8. filtrationThe white precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-880336a7f2bd41f285555f722e87b84a
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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