Acetic Anhydride → HCID 59434284, compound

HRID 507858Notes

Reaction equation

HRID 507858 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23](OC(C)=O)=[O:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:23](=[O:24])[CH3:22])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 16413902tert-Butyl 4-(4-fluoroanilino)piperidine-1-carboxylate

Product 1

HCID 59434284HCID 59434284, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(4-Fluoro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.8 g; 9.51 mmol; 1 eq.) was dissolved in DCM (30 mL) and Ac2O (2.2 mL; 23.77 mmol; 2.5 eq.) was added. DMAP (1.51 g; 12.36 mmol; 1.3 eq.) was introduced and the reaction was stirred overnight (approx. 18 hours) at room temperature. The solution was diluted with DCM (150 mL) and washed with 1N HCl (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under high vacuum to provide the product as an oil. The crude product was used without further purification. LC/MS M/Z 337.3, Retention time=2.95 minutes; 10-99% CH3CN/H2O gradient with 0.05% TFA). H NMR (400 MHz, CDCl3) δ7.16-7.05 (m, 4H), 4.77 (tt, J=12.2 Hz, 3.8 Hz, 1H), 4.13 (d, J=7.1 Hz, 2H), 2.81 (t, J=12.4 Hz, 2H), 1.82-1.73 (m, 2H), 1.77 (s, 3H), 1.41 (s, 9H), 1.26-1.16 (m, 2H).

Workup

  1. washwashed with 1N HCl (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-f5b40fa989284978876df3e7eb1ea133
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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