Piperazine → o-Phenetidine

HRID 1292840

Reaction equation

HRID 1292840 reaction equation
N1CCNCC1.BrCCOC(=O)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH3:21].[N-]=C=O>CN(C=O)C>[CH2:20]([O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH2:12])[CH3:21]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 105034IsocyanateHCID 111620142-bromoethyl-N-(2-ethoxyphenyl)carbamate

Product 1

HCID 7203o-Phenetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 μl of TEA (0.033 mmol, 1.1 eq) is added then 500 μl of piperazine (0.03 mmol, 1 eq) dissolved in DMF to 300 μl of 0.2 M 2-bromoethyl-N-(2-ethoxyphenyl)carbamate (0.06 mmol, 2 eq) dissolved in DMF. After 18 hours at room temperature and evaporation of the solvents, the mixtures are taken up in 1 ml of CH2Cl2 and treated with isocyanate resin (Argonaut, 1.51 mmol/g, 0.09 mmol/g, 0.09 mmol, 3 eq) for 18 hours. Next, the mixtures are purified on cation exchange resins according to the protocol described hereinabove. The desired compounds are then obtained after elimination of the solvents.

Workup

  1. customevaporation of the solvents
  2. customNext, the mixtures are purified on cation exchange resins

Sources & evidence

ORD record
ord-29cfcdddbd9f4490814f1268c90c7ff3
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Linked notes

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