Acetic Acid → HCID 12168335, compound

HRID 343145Notes

Reaction equation

HRID 343145 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C1COCC1>[CH:10]1([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7732P-AnisidineHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12168335HCID 12168335, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7.00 g (56.8 mmol) p-Anisidine, 9.56 g (114 mmol, 2.0 equiv) Cyclopentanone, and 4.10 g (68.2 mmol, 1.2 equiv) Acetic acid in 145 mL Methanol is added 125 mL (125 mmol, 2.2 equiv) 1N Sodium cyanoborohydride in THF and stirred 18 h at ambient temperature. The reaction mixture is concentrated in vacuo and the residue taken into 200 mL EtOAc, washed with H2O (150 mL), dried (MgSO4), filtered and concentrated in vacuo to give crude Cyclopentyl-(4-methoxy-phenyl)-amine as a brown oil. To a stirred solution of this material and 6.03 g (58.6 mmol, 1.05 equiv) Et3N in 70 mL DCM is added 11.47 g (56.8 mmol, 1 equiv) Bromoacetyl bromide in 50 mL DCM dropwise over 30 minutes at 0° C. The reaction mixture is stirred 1 h at 0° C. followed by warming to ambient temperature and stirring 18 h. The reaction mixture is washed with 1N HCl (3×50 mL), dried (MgSO4), filtered through a pad of 100 g silica gel eluted with EtOAc/Hexanes (3:17, 1.5 L), and concentrated in vacuo to give 10.22 g (32.7 mmol) of 2-Bromo-N-cyclopentyl-N-(4-methoxy-phenyl)-acetamide as an orange oil: 1H NMR (CDCl3, 300 MHz) δ7.09 (d, 2H, J=9.0), 6.90 (d, 2H, J=9.0), 4.84 (m,1H), 3.83 (s, 3H), 3.54 (s, 2H), 1.87 (m, 2H), 1.49 (m, 4H), 1.25 (m, 2H); TLC Rf =0.65 (EtOAc/Hexanes, 3:17).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washwashed with H2O (150 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54fc6a0dc9f3469ab9ed42e1484ab54a
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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