Phenyl chloroformate → HCID 70577728, compound

HRID 2286910Notes

Reaction equation

HRID 2286910 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].C[N:12]1[CH2:17][CH2:16][C:15]2([C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:24][C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:13]1>C(Cl)Cl>[O:4]([C:2]([N:12]1[CH2:13][CH2:14][C:15]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[O:24][C:25]3[C:30]2=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:16][CH2:17]1)=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 14570248HCID 14570248, compound

Product 1

HCID 70577728HCID 70577728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phenyl chloroformate (8 ml.) in methylene chloride (75 ml.) is added dropwise with stirring to a solution of 1'-methylxanthene-9-spiro-4'-piperidine (17.0 g.) in methylene chloride (200 ml.) at 5° C. The mixture is allowed to reach room temperature and stirred overnight. The mixture is washed successively with 3 N sodium hydroxide solution, 3 N hydrochloric acid and water, dried (MgSO4) and the methylene chloride evaporated to dryness. The gummy residue is crystallised from methanol to give 1'-phenoxycarbonylxanthene-9-spiro-4'-piperidine, m.p. 105°-107° C.

Workup

  1. customto reach room temperature
  2. washThe mixture is washed successively with 3 N sodium hydroxide solution, 3 N hydrochloric acid and water
  3. dry with materialdried (MgSO4)
  4. customthe methylene chloride evaporated to dryness
  5. customThe gummy residue is crystallised from methanol

Sources & evidence

ORD record
ord-0bb1012970a14c6a8ba3c1e623b6ddd8
Source dataset
uspto-grants-1981_05
Patent number
US04268514

Reaction notes

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