Pyridine → (1-(Pyridin-4-YL)piperidin-4-YL)methanol

HRID 987512Notes

Reaction equation

HRID 987512 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[OH:17][CH2:16][CH:13]1[CH2:14][CH2:15][N:10]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 4207714-PiperidinemethanolHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanolYield 70%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The mixture of 4-pyridineboronic acid (0.97 g, 7.8 mmol), 4-piperidinemethanol (1.82 g, 15.8 mmol), Cu(OAc)2 (2.88 g, 15.8 mmol), DMAP (catalytic amount), pyridine (2.5 mL, 32 mmol), 4A activated molecular sieve in 50 mL dry DCM was stirred for over 2 days. It was diluted with DCM, filtered through celite. It was washed with brine and water, dried, filtered through a silica plug, evaporated in vacuuo to give 4-(4-hydroxylmethylpiperidin-1-yl)pyridine in 70% yield. ES-MS: (M+H)+193.

Workup

  1. filtrationfiltered through celite
  2. washIt was washed with brine and water
  3. customdried
  4. filtrationfiltered through a silica plug
  5. customevaporated in vacuuo

Sources & evidence

ORD record
ord-d30059627acc4ca58f3224a236c2204a
Source dataset
uspto-grants-2003_10
Patent number
US06632815B2

Reaction notes

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