Dichloromethane → HCID 19599744, compound

HRID 609655Notes

Reaction equation

HRID 609655 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:20](=[O:23])[CH2:21]Br)[CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[C:14]1([CH:12]([CH3:13])[CH2:11][N:10]2[CH2:9][CH2:8][NH:7][CH2:21][C:20]2=[O:23])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67574624HCID 67574624, compound

Product 1

HCID 19599744HCID 19599744, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same way as that described in Example 2, Step 3, using 2-[(bromoacetyl)(2-phenylpropyl)amino]ethyl carbamic acid tert-butyl ester (1.64 g, 4.11 mmol), trifluoroacetic acid (4 mL) and CH2Cl2 (40 mL), followed by K2CO3 (1.1 g, 8.2 mmol) and EtOH (100 mL). The piperazinone (668 mg, 75%) was isolated as a colourless oil. 1H NMR (250 MHz, CDCl3) δ1.28 (3H, d, J=6.8 Hz), 2.72-2.93 (3H, m), 3.04-3.26 (3H, m), 3.28 (1H, d, J=17.3 Hz), 3.52 (1H, d, J=17.3 Hz), 3.85-3.93 (1H, m), 7.19-7.35 (5H, m).

Sources & evidence

ORD record
ord-3cf4fa0bf3e541298c06237e04e6ba55
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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