Pyridine → 4-(4-Boc-aminopiperidin-1-yl)pyridine

HRID 987509Notes

Reaction equation

HRID 987509 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[C:10]([CH:17]1[CH2:22][CH2:21][N:20](N)[CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[N:24]1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:10]([CH:17]1[CH2:22][CH2:21][N:20]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:19]([NH2:24])[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

7

Reactant 3

HCID 1049PyridineHCID 2734379(Pyridin-4-yl)boronic acidHCID 21899493Tert-butyl 1-aminopiperidine-4-carboxylate

Product 1

HCID 698900834-(4-Boc-aminopiperidin-1-yl)pyridineYield 90%

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-Boc-aminopiperidine (3.25 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-Boc-aminopiperidin-1-yl)pyridine in 90% yield. ES-MS: (+H) 278.

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-81c103d1ec7547f2a469529aae0b410b
Source dataset
uspto-grants-2003_10
Patent number
US06632815B2

Reaction notes

Loading…