Hydrochloric Acid → 4-Methyl-4-aza-7-azoniaspiro[2.5]octane, dihydrochloride

HRID 1366576Notes

Reaction equation

HRID 1366576 reaction equation
[CH3:1][N:2]1[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6][C:3]21[CH2:5][CH2:4]2.[ClH:17]>CO>[ClH:17].[ClH:17].[CH3:1][N:2]1[CH2:9][CH2:8][NH2+:7][CH2:6][C:3]21[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 669360794-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane

Product 1

HCID 1317287134-Methyl-4-aza-7-azoniaspiro[2.5]octane, dihydrochlorideYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane (1.43 g, 6.624 mmol) was dissolved in 10 mL of MeOH, degassed and placed under argon. Pd(OH)2 (140 mg) was added, and the contents were hydrogenated for 4 h under 50 psi. The contents were then filtered to remove the catalyst, 1N HCl (14.57 mL, 14.57 mmol) was added to the filtrate, and the filtrate was concentrated in vacuo to provide pure 4-methyl-4-aza-7-azoniaspiro[2.5]octane, dihydrochloride (0.8 g, 60%). LCMS: (M+H)+: 127.2.

Workup

  1. customdegassed
  2. additionPd(OH)2 (140 mg) was added
  3. filtrationThe contents were then filtered
  4. additionwas added to the filtrate
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0b6f1ce512e641a283477fa652fadba5
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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