Aniline → HCID 51204633, compound

HRID 1157800Notes

Reaction equation

HRID 1157800 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1.O.Cl.C(OCC)(=O)C>[C:30]1([NH:29][C:12]([CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:16][CH2:15]2)=[O:14])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 3

HCID 6115AnilineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 51204633HCID 51204633, compoundYield 65.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Part A: To a solution of N-Boc-isonipecotic acid (4.85 g, 21.2 mmol) in tetrahydrofuran (80 mL) at 25° C. was added carbonyl diimidazole (3.80 g, 23.3 mmol), and the reaction mixture was stirred for 1.00 h at 25° C. To the resulting mixture was added aniline (2.10 mL, 23.3 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) (3.20 mL, 21.2 mmol), and the solution was stirred at 25° C. for another 90 h. The reaction mixture was diluted with water, 1.00 N hydrochloric acid (80 mL), and ethyl acetate. The phases were separated, and the organic phase was washed with water (×2) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% diethyl ether/methylene chloride) furnished tert-butyl 4-(phenylcarbamoyl)-piperidine-1-carboxylate (4.25 g) as a white solid; 1H NMR (300 MHz, CDCl3) δ 7.48 (d, 2H, J=8.0 Hz), 7.29 (t, 2H, J=8.0 Hz), 7.20 (br s, 1H), 7.08 (t, 1H, J=8.0 Hz), 4.16 (m, 2H), 2.75 (m, 2H), 2.35 (m, 1H), 1.89-1.61 (m, 4H), 1.43 (s, 9H).

Workup

  1. stirringthe solution was stirred at 25° C. for another 90 h
  2. customThe phases were separated
  3. washthe organic phase was washed with water (×2) and brine
  4. customdried over anhyd
  5. filtrationsodium sulfate, filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db65a70426d24be09f85eb2dc80bdbf6
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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