Acetic Anhydride → 1-(5-Bromopyridin-2-yl)piperidin-4-yl acetate

HRID 447303Notes

Reaction equation

HRID 447303 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl.[Cl-].[Na+].O>[C:15]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:9][CH2:10]1)(=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218978371-(5-Bromopyridin-2-yl)piperidin-4-ol

Product 1

HCID 667304631-(5-Bromopyridin-2-yl)piperidin-4-yl acetate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(5-bromopyridin-2-yl)piperidin-4-ol (200 mg, 0.78 mmol), acetic anhydride (0.16 mL, 1.7 mmol), DMAP (10 mg, 0.08 mmol), and Et3N (0.24 mL, 1.7 mmol) in CH2Cl2 (4 mL) was stirred at rt for 17 h. Brine was added and extracted with CH2Cl2, dried over MgSO4, filtered and concentrated to dryness. The crude product was triturated with water and the title compound was collected by vacuum filtration (203 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 8.17 (d, J=2.2 Hz, 1H), 7.52 (dd, J=9.0 Hz, 2.5 Hz, 1H), 6.57 (d, 9.0 Hz, 1H), 5.01-4.95 (m, 1H), 3.9-3.85 (m, 2H), 3.35-3.28 (m, 2H), 2.07 (s, 3H), 1.99-1.92 (m, 2H), 1.74-1.65 (m, 2H); MS ESI 300.9 [M+H]+, calcd for [C12H15BrN2O2+H]+ 299.03.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was triturated with water
  6. filtrationthe title compound was collected by vacuum filtration (203 mg, 88%)

Sources & evidence

ORD record
ord-67179bc1b37d4010b3f9a7269b4850d4
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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