N-Piperidin-4-ylidenehydroxylamine → HCID 178511976, compound

HRID 1464113Notes

Reaction equation

HRID 1464113 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]#[N:9].[NH:16]1[CH2:21][CH2:20][C:19](=[N:22][OH:23])[CH2:18][CH2:17]1>C(O)C>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([N:16]1[CH2:21][CH2:20][C:19](=[N:22][OH:23])[CH2:18][CH2:17]1)=[NH:9]

Participants

4

Reactant 2

HCID 12849639N-Piperidin-4-ylidenehydroxylamineHCID 190892212-Biphenylylcyanamide

Product 1

HCID 178511976HCID 178511976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-biphenylylcyanamide (3.9 g), 4-piperidone oxime (4.5 g) and ethanol (50 ml) was stirred at ambient temperature for 6 hours and then at 50°-60° C. for 5 hours to give a brown solid which was purified by chromatography on an aluminia column eluted successively with hexane, 1:4, 2:3, 3:2 and 4:1 mixtures of dichloromethane and hexane and the 99:1 mixture of dichloromethane and methanol to yield a solid which was recrystallised from ethyl acetate to give N-(2-biphenylyl)-4-hydroxyiminopiperidine-1-carboxamidine (m.p. 175°-176° C.).

Workup

  1. customat 50°-60° C. for 5 hours to give a brown solid which
  2. customwas purified by chromatography on an aluminia column
  3. washeluted successively with hexane, 1:4, 2:3, 3:2 and 4:1 mixtures of dichloromethane and hexane
  4. additionthe 99:1 mixture of dichloromethane and methanol
  5. customto yield a solid which
  6. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-465a9d0715a04f54ba8dd0c1e2445d0f
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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