Ethanol → HCID 22029155, compound

HRID 1829167Notes

Reaction equation

HRID 1829167 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].C(O)C.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]#[N:25])[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.Cl.C(N1N=NC(C2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)=N1)(C)(C)C>C(Cl)(Cl)Cl>[ClH:4].[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([O:3][CH2:1][CH3:2])=[NH:25])[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylateHCID 67508035HCID 67508035, compound

Product 1

HCID 22029155HCID 22029155, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Acetyl chloride (180 mL) was dropwise added to a mixture of ethanol (160 mL) and chloroform (180 mL) under ice-cooling. After the mixture was stirred for 30 min, a solution of 1-benzyloxycarbonyl-4-cyanopiperidine [product of Example 298 (2), 20.6 g] in chloroform (180 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure to give 1-benzyloxycarbonyl-4-(ethoxycarbonimidoyl)piperidine hydrochloride (28.7 g) as a white solid.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringThe mixture was stirred at room temperature for 18 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45e9858145a147bf86da19d5a4123db0
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

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