Methanol → HCID 18915248, compound

HRID 1017542Notes

Reaction equation

HRID 1017542 reaction equation
[ClH:1].[C:2]1(=O)[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.[CH3:13][N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)N.CO>Cl>[ClH:1].[CH3:13][N:14]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:3]2[CH2:4][CH2:5][C:6]3([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]3)[C:2]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 36299N-methyl-N-phenyl-hydrazineHCID 184039658-Azaspiro[4,5]decane-1-one hydrochloride

Product 1

HCID 18915248HCID 18915248, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 8-azaspiro[4,5]decane-1-one hydrochloride (5.2 g) in 95% ethanolic hydrochloric acid (30 ml) and 1-methyl-1-phenylhydrazine (5 g) was heated overnight on a steam bath, under nitrogen. The reaction mixture was cooled to ambient temperature, methanol was added and the mixture was concentrated in vacuo. The residue was flash chromatographed (silica gel) eluting with 10% methanol/dichloromethane. The appropriate fractions were collected and concentrated to afford 7.4 g (95%) of product, mp>270° C.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customchromatographed (silica gel)
  3. washeluting with 10% methanol/dichloromethane
  4. customThe appropriate fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1ea8d8d0d9c422297089db43acf0088
Source dataset
uspto-grants-2002_11
Patent number
US06479501B2

Reaction notes

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