Cyanamide → HCID 86611690, compound

HRID 747092Notes

Reaction equation

HRID 747092 reaction equation
C([CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#N.[C:23]([NH2:25])#[N:24]>C1COCC1.O=[Mn]=O>[NH:25]([CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])[CH2:8][CH2:9]1)[C:23]#[N:24]

Participants

5

Reactant 2

HCID 9864Cyanamide2×HCID 45926010tert-Butyl 4-[cyano(phenyl)methyl]piperazine-1-carboxylate

Product 1

HCID 86611690HCID 86611690, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An excess amount of NiO2—H2O (25 g) was added into a solution of tert-butyl 4-(cyano(phenyl)methyl)piperazine-1-carboxylate (10 g) and cyanamine (7 g) in THF (100 ml). An additional cyanamine (25 g) and MnO2 (100 g) was added after 24 hours, and then the reaction was kept stirring for 5 days. The solids were removed by filtration. The filtrate was concentrated under vaccum to give a residue which was purified by silica gel column chromatography to provide tert-butyl 4-(cyanamido(phenyl)methyl)piperazine-1-carboxylate.

Workup

  1. customThe solids were removed by filtration
  2. concentrationThe filtrate was concentrated under vaccum
  3. customto give a residue which
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b421e1c618a4fb2806c709a5721517d
Source dataset
uspto-grants-2008_07
Patent number
US07396830B2

Reaction notes

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