Methanol → HCID 18915248, compound

HRID 1292459Notes

Reaction equation

HRID 1292459 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-c7e7ad48a6ea4fc9ada8a78ba5b0e09d
Source dataset
uspto-grants-1998_05
Patent number
US05756743

Reaction notes

Loading…