HCID 22254655, compound → HCID 22254643, compound

HRID 1611660Notes

Reaction equation

HRID 1611660 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[NH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1)([O-])=O>[Ni].C1COCC1>[NH2:1][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[NH:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 22254655HCID 22254655, compound

Product 1

HCID 22254643HCID 22254643, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of Raney nickel (510 mg) in THF (40 ml) was added 2-nitro-1-N-[1-(phenylmethyloxycarbonyl)-piperidin-4-yl]aniline (Method D) (200 mg, 0.56 mmol) and the mixture was stirred under a hydrogen atmosphere (1 atmosphere). After 15 h the mixture was filtered through Celite™, concentrated and purified by column chromatography (eluting with 25% EtOAc/DCM) to give the title compound as an oil (50 mg, 0.15 mmol); NMR: 1.3 (m, 2H), 1.9 (m, 2H), 3.0 (m, 2H), 3,3 (m, 2H),3.9 (m, 1H), 4.1 (d, 1H), 4.45 (br s, 2H), 5.05 (s, 2H), 6.4 (m, 4H) and 7.3 (m, 5H); MS: 326.

Workup

  1. filtrationAfter 15 h the mixture was filtered through Celite™
  2. concentrationconcentrated
  3. custompurified by column chromatography (eluting with 25% EtOAc/DCM)

Sources & evidence

ORD record
ord-3bc82d20d2414bda907cd27ad39f0c6f
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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