Nitrourea → HCID 54520210, compound

HRID 443301Notes

Reaction equation

HRID 443301 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([NH:27][C:28](N)=[O:29])([O-])=O>O.C(#N)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][NH:15][C:28]([NH2:27])=[O:29])([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 62372NitroureaHCID 21193317HCID 21193317, compound

Product 1

HCID 54520210HCID 54520210, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzyl-4-(3-methylphenylamino)-4-aminomethylpiperidine (247 mg, 0.79 mmol) and nitrourea (253 mg, 2.4 mmol) in mixture of acetonitrile (1 mL) and water (10 drops) was stirred at room temp. for 48 hrs. The resultant mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of 15% methanol in chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. additionthe residue was subjected to column chromatography on silica gel eluting with a 1:1 mixture of 15% methanol in chloroform and chloroform saturated with ammonia gas
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-ae8469236e3e44f1b9e23e41a8a198de
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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