Chlorosuccinimide → HCID 70579239, compound

HRID 1414570Notes

Reaction equation

HRID 1414570 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5][CH2:4]1.[Cl:22]N1C(=O)CCC1=O>ClCCl>[ClH:22].[Cl:1][C:11]1[CH:12]=[CH:13][C:14]2[O:15][C:16]3[C:21]([C:6]4([CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]4)[C:9]=2[CH:10]=1)=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 14570249HCID 14570249, compound

Product 1

HCID 70579239HCID 70579239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1'-methylxanthene-9-spiro-4'-piperidine hydrochloride (5 g.), N-chlorosuccinimide (4.5 g.) and dichloromethane (100 ml.) is refluxed for 72 hours. The solution is washed with saturated sodium bicarbonate solution then water and dried with MgS04. The solution is evaporated to give a gummy residue which is chromatographed on grade 3 aluminium oxide, Woelm basic. The product is eluted with 30% petroleum-ether (b.p. 60°-80° C.)/chloroform, taken up in ether and the solution treated with ethereal hydrochloric acid. The precipitate is filtered and recrystallised from ethanol-ether to give 2,7-dichloro-1'-methylxanthene-9-spiro-4'-piperidine hydrochloride, m.p. 285° C.

Workup

  1. temperatureis refluxed for 72 hours
  2. washThe solution is washed with saturated sodium bicarbonate solution
  3. dry with materialwater and dried with MgS04
  4. customThe solution is evaporated
  5. customto give a gummy residue which
  6. customis chromatographed on grade 3 aluminium oxide, Woelm basic
  7. washThe product is eluted with 30% petroleum-ether (b.p. 60°-80° C.)/chloroform
  8. additionthe solution treated with ethereal hydrochloric acid
  9. filtrationThe precipitate is filtered
  10. customrecrystallised from ethanol-ether

Sources & evidence

ORD record
ord-c02a14a100ae4b90a748002859301f20
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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