Methyl chloroformate → HCID 15020371, compound

HRID 1460255Notes

Reaction equation

HRID 1460255 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:31]([O:33][CH3:34])=[O:32]>C(Cl)Cl>[CH3:34][O:33][C:31]([N:15]1[CH2:16][CH2:17][CH:12]([C:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([NH2:11])=[O:10])[CH2:13][CH2:14]1)=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 15020370HCID 15020370, compound

Product 1

HCID 15020371HCID 15020371, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of α,α-bis(4-fluorophenyl)-4-piperidineacetamide (7.65 g, 0.023 mol) and sodium bicarbonate (3.36 g, 0.023 mole) in methylene chloride was prepared. To this mixture was added a solution of methyl chloroformate (2.17 g, 0.023 mole) in methylene chloride. The resulting mixture was stirred overnight at room temperature. The mixture was extracted successively with water, 5% sodium hydroxide, and water. The methylene chloride layer was dried (sodium sulfate). The organic layer was filtered, and solvent was removed to provide a fluffy, white residue (5.95 g, 66.6% yield). A 0.5 g sample was crystallized from methylene chloridehexanes. This provided a white solid which was dried in vacuo overnight at 80° C., mp 126°-129° C.

Workup

  1. customwas prepared
  2. extractionThe mixture was extracted successively with water, 5% sodium hydroxide, and water
  3. dry with materialThe methylene chloride layer was dried (sodium sulfate)
  4. filtrationThe organic layer was filtered
  5. customsolvent was removed

Sources & evidence

ORD record
ord-fb7621407c4e480a93e1f8d157162b19
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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