Piperidin-4-ol → HCID 69277538, compound

HRID 1504589Notes

Reaction equation

HRID 1504589 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1>CCN(C(C)C)C(C)C>[OH:17][CH:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 804566-Chloronicotinamide

Product 1

HCID 69277538HCID 69277538, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
110 °C

Procedure

To the solution of 6-chloronicotinamide (5.0 g, 32 mmol) in DIPEA (50 mL), piperidin-4-ol (3.2 mg, 32 mmol) was added and the mixture was stirred at 110° C. for 8 h. The reaction mixture was concentrated under reduced pressure to afford the crude product. The residue was further purified by silica gel chromatography (DCM: MeOH=20:1) to afford the title compound (5.3 g, 75%) as a yellowish solid. [LCMS RtB=1.39 min, [M+H]+=222.1].

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude product
  3. customThe residue was further purified by silica gel chromatography (DCM: MeOH=20:1)

Sources & evidence

ORD record
ord-88dc13fef20948749c6d513f6cec1e0c
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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