Dichloromethane → HCID 19599740, compound

HRID 609650Notes

Reaction equation

HRID 609650 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:21](=[O:24])[CH2:22]Br)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[F:20][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][N:10]2[CH2:9][CH2:8][NH:7][CH2:22][C:21]2=[O:24])[CH:18]=[CH:17][C:16]=1[F:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67574634HCID 67574634, compound

Product 1

HCID 19599740HCID 19599740, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same way as that described in Example 2, Step 3 using 2-[(bromoacetyl)(2-(3,4-difluorophenyl)ethyl)amino]ethyl carbamic acid tert-butyl ester (549 mg, 1.3 mmol), trifluoroacetic acid (2.5 mL) and CH2Cl2 (25 mL), followed by K2CO3 (0.36 g, 2.6 mmol) and EtOH (50 mL). The piperazinone (286 mg, 91%) was isolated as a yellow oil. 1H NMR (250 MHz, CDCl3) δ 2.85 (2H, t, J=7.3Hz), 2.99-3.03 (2H, m), 3.17-3.21 (2H, m), 3.52 (2H, s), 3.56 (2H, t, J=7.3Hz), 6.90-7.16 (3H, m). MS (ES+) (241, M+1).

Sources & evidence

ORD record
ord-3320b7b8651a4e15941e6dea9d9e5589
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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