1,1-Dimethylethyl 4-[4-[[[1-(2-methoxy-2-oxoethyl)-4-piperidinyl]carbonyl]amino]phenyl]-1-piperazinecarboxylate → HCID 15886541, compound

HRID 1108660Notes

Reaction equation

HRID 1108660 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:25][CH2:24]3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([CH:23]3[CH2:24][CH2:25][N:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:28]3)=[O:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 700709071,1-Dimethylethyl 4-[4-[[[1-(2-methoxy-2-oxoethyl)-4-piperidinyl]carbonyl]amino]phenyl]-1-piperazinecarboxylate

Product 1

HCID 15886541HCID 15886541, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of Methyl 4-[[[4-(4-t-butyloxycarbonyl-1-piperazinyl)phenyl]amino]carbonyl]-1-piperidine acetate (2.1 g, 4.5 mmol) was treated with CH2Cl2 /TFA (10 mL/15 mL) for 20 min. Solution was concentrated and the residue was treated with MeOH/4M HCl (10 mL/10 mL). Solution was concentrated until precipitation started. Solution was filtered and the solid was washed with Et2O to give the title compound (1.5 g, 87%). MS (ES) m/e 361 [M+H]+. 1HNMR (250 MHz, DMSO[d6]) δ 1.4-4.5 (m, 22H), 6.9-9.5 (m, 5H). Anal. (C18H25N3O3.2.87HCl.0.5H2O) calcd: C, 54.32; H, 7.20; N, 10.29. found: C, 54.52; H, 7.24; N, 10.35.

Workup

  1. concentrationSolution was concentrated
  2. additionthe residue was treated with MeOH/4M HCl (10 mL/10 mL)
  3. concentrationSolution was concentrated until precipitation
  4. filtrationSolution was filtered
  5. washthe solid was washed with Et2O

Sources & evidence

ORD record
ord-bd17f749077f40ebb180bbd1ce15ba33
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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