Dimethylformamide → HCID 86635668, compound

HRID 2388685Notes

Reaction equation

HRID 2388685 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C.CCCCCC>[Cl:3][C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][C:13]=1[CH:9]=[O:10]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 86635668HCID 86635668, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

POCl3 (26.35 g, 16.06 ml, 1.6 eq.) was added dropwise to DMF (16.4 ml, 2 eq.) at 0-5° C. To the mixture was added dichloromethane (50 ml) in a dropwise fashion and it was stirred for 2 h at room temperature. A solution of benzyl 4-oxopiperidine-1-carboxylate (25 g, 0.10 mol) in dichloromethane (200 ml) was added dropwise to the mixture and it was stirred for 2 h at room temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane). Upon completion of the reaction the mixture was poured into crushed ice and basified to a pH˜8 with sodium carbonate. Then the dichloromethane layer was separated and the aqueous layer was extracted with dichloromethane (2×200 ml). The combined organic layers were dried over sodium sulfate, concentrated under reduced pressure and the crude product obtained was purified by column chromatography (silica, 8% ethyl acetate/hexane). Yield: 14.5 g (48%).

Workup

  1. stirringwas stirred for 2 h at room temperature
  2. customUpon completion of the reaction the mixture
  3. additionwas poured
  4. custominto crushed ice
  5. customThen the dichloromethane layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×200 ml)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eefe1ac229c64d78932f207dd2505b1f
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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