Piperidin-4-ol → HCID 69556362, compound

HRID 1168320Notes

Reaction equation

HRID 1168320 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>CN(C1C=CN=CC=1)C>[CH3:9][NH:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:16]2[CH2:17][CH2:18][CH:13]([OH:12])[CH2:14][CH2:15]2)=[N:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 123642306-Chloro-N-methylnicotinamide

Product 1

HCID 69556362HCID 69556362, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 8.51 g (49.9 mmol) 6-chloro-N-methyl-nicotinamide, 5.66 g (54.9 mmol) 4-hydroxypiperidine, 26.1 ml (150 mmol) N-ethyldiisopropylamine and 0.31 g (2.5 mmol) 4-(N,N-dimethylamino)-pyridine was heated at reflux over night. After cooling to room temperature the crude mixture was transferred to a flash chromatography column. Elution afforded 10.1 g (86.1%) of the title compound as a light yellow solid. MS m/e (%): 236 (M+H+, 100).

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. washElution

Sources & evidence

ORD record
ord-274355226727448c9ff8930c171317ab
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

Loading…