Acetyl chloride → 2-(Pyridin-4-yl)-2,8-diazaspiro[4.5]decane dihydrochloride

HRID 1253711Notes

Reaction equation

HRID 1253711 reaction equation
C([Cl:4])(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[CH2:12]2)=[CH:7][CH:6]=1>C(O)C>[ClH:4].[ClH:4].[N:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59486376Tert-butyl 2-(pyridin-4-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 667007962-(Pyridin-4-yl)-2,8-diazaspiro[4.5]decane dihydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (5 eq.) was added to an ice-cold solution of tert-butyl 2-(pyridin-4-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (3.78 mmol, 1 eq.) in ethanol (14 ml). The reaction mixture was stirred at room temperature overnight. The solvent was concentrated in vacuo and the residue was dissolved in ethanol/acetone (2:1, 30 ml). The white solid which precipitated was filtered out, washed with diethyl ether and dried in vacuo. Yield: 98%

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethanol/acetone (2:1, 30 ml)
  3. customThe white solid which precipitated
  4. filtrationwas filtered out
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6cd6dcd1cea8402da3de6500dd1ca43f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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