Sodium Acetate → 3-Chloro-5-isopropyl-azepan-2-one

HRID 851978Notes

Reaction equation

HRID 851978 reaction equation
[Cl:1][C:2]1(Cl)[CH2:8][CH:7]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:5][NH:4][C:3]1=[O:12].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][CH:2]1[CH2:8][CH:7]([CH:9]([CH3:10])[CH3:11])[CH2:6][CH2:5][NH:4][C:3]1=[O:12]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 694911453,3-Dichloro-5-isopropyl-azepan-2-one

Product 1

HCID 694913233-Chloro-5-isopropyl-azepan-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,3-Dichloro-5-isopropyl-azepan-2-one (5.00 g, 22.3 mmol) was dissolved in acetic acid (125 ml) and sodium acetate (anhydrous, 2.38 g, 29.0 mmol), 10% Pd-c catalyst (0.22 g) were added. The degassed mixture was hydrogenated at r.t. and atmospheric pressure for 90 min. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified over silica gel (ethyl acetate/n-heptane 1:1): 3.49 g (74%) 1H NMR (CDCl3) δ 0.88-0.90 (m, 6H), 1.26-1.29 (m, 1H), 1.63-1.67 (m, 2H), 1.76-1.94 (m, 2H), 2.16-2.21 (m, 1H), 3.19-3.23 (m, 1H), 3.30-3.36 (m, 1H), 4.64 & 4.67 (dd, 1H), 6.45 (br, 1H) MS: m/e=190.3 (MH+), 207.2 (MNH4+)

Workup

  1. customwas hydrogenated at r.t.
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over silica gel (ethyl acetate/n-heptane 1:1)

Sources & evidence

ORD record
ord-fb4fae90c2764494961ddd8b9fe21f52
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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