4-(1,4-Dioxaspiro[4.5]dec-8-ylamino)-3-methoxy-2-methylpyridine hydrochloride → 4-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridine hydrochloride

HRID 1005

Reaction equation

HRID 1005 reaction equation
[ClH:1].O1[C:6]2([CH2:11][CH2:10][CH:9]([NH:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[C:14]=3[O:20][CH3:21])[CH2:8][CH2:7]2)[O:5]CC1>C(O)=O>[ClH:1].[O:5]=[C:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[C:14]=2[O:20][CH3:21])[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 196940114-(1,4-Dioxaspiro[4.5]dec-8-ylamino)-3-methoxy-2-methylpyridine hydrochloride

Product 1

HCID 196939634-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

27.3 g of 4-(1,4-dioxaspiro[4.5]dec-8-ylamino)-3-methoxy-2-methylpyridine hydrochloride are stirred with 400 ml of formic acid for 4 hours. The residue which remains after concentrating in vacuo is dissolved in methylene chloride and shaken with 2N NaOH. The methylene chloride phase is concentrated, the residue is dissolved in ether and the hydrochloride is precipitated by addition of ethereal HCl. 14 g=90%; m.p.: 115° to 120° C.

Workup

  1. concentrationafter concentrating in vacuo
  2. dissolutionis dissolved in methylene chloride
  3. concentrationThe methylene chloride phase is concentrated
  4. dissolutionthe residue is dissolved in ether
  5. customthe hydrochloride is precipitated by addition of ethereal HCl

Sources & evidence

ORD record
ord-87cd3f597261426bbf9068b66cd80964
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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