Water → 1-Amino-cyclohexanecarboxylic acid cyanomethyl amide

HRID 478617Notes

Reaction equation

HRID 478617 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:30])[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)=[O:6])#[N:2].N1CCCCC1.O.C(Cl)Cl.CO>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:30])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 21226129Dichloromethane methanolHCID 86583639FMOC-1-amino-cyclohexanecarboxylic acid cyanomethyl-amide

Product 1

HCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

FMOC-1-amino-cyclohexanecarboxylic acid cyanomethyl-amide (248 mmol) is dissolved in DMF (200 ml), piperidine (248 mmol) is added and the mixture is stirred at RT for 2 hours. The reaction mixture is poured into water (3000 ml) and stirred for 30 minutes. The suspension is filtered and the filtrate is acidified with HCl 4N and than extracted with ethyl acetate. NaOH 1N is added to make the water phase basic and the mixture is extracted three times with ethyl acetate. The organic fractions are dried over sodium sulfate and the solvent is evaporated. The residue is dried (vacuum) to yield a pale yellow oil. Rf=0.26 (CH2Cl2/MeOH=95:5).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe suspension is filtered
  3. extractionthan extracted with ethyl acetate
  4. additionNaOH 1N is added
  5. extractionthe mixture is extracted three times with ethyl acetate
  6. dry with materialThe organic fractions are dried over sodium sulfate
  7. customthe solvent is evaporated
  8. customThe residue is dried (vacuum)
  9. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-fb7317789f494d9796c956f7e4e9b105
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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