Hydrochloric Acid → 2,4-Dichloro-N-{[1-(cyclopropylmethyl)-4-oxocyclohexyl]methyl}benzamide

HRID 2263602Notes

Reaction equation

HRID 2263602 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1)=[O:5].Cl.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([CH2:18][CH:19]2[CH2:20][CH2:21]2)[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 686824732,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

Product 1

HCID 686831652,4-Dichloro-N-{[1-(cyclopropylmethyl)-4-oxocyclohexyl]methyl}benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-N-[(8-cyclopropylmethyl-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide (11 g; 27.6158 mmol) was dissolved in THF (80 ml) and HCl (2M; 80 ml) and the solution stirred at ambient temperature for 18 hours. The solution was adjusted to pH 9 with 10N NaOH solution and extracted with DCM (2×75 ml). The combined organics were dried (MgSO4) filtered and evaporated to give an oil which was crystallised from EtOAc isohexane as a white solid (8.0 g) 1H NMR δ (ppm) (CDCl3): 7.67 (1 H, d, J=8.3 Hz), 7.44 (1 H, d, J=2.0 Hz), 7.34 (1 H, dd, J=2.0, 8.3 Hz), 6.37 (1 H, s), 3.72 (2 H, d, J=6.4 Hz), 2.57-2.49 (2 H, m), 2.39-2.31 (2 H, m), 1.92-1.80 (4 H, m), 1.43 (2 H, s), 0.77-0.69 (1 H, m), 0.58-0.54 (2 H, m), 0.11 (2 H, q, J=5.0 Hz). MS (m/e)=354.

Workup

  1. extractionextracted with DCM (2×75 ml)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil which
  6. customwas crystallised from EtOAc isohexane as a white solid (8.0 g) 1H NMR δ (ppm) (CDCl3): 7.67 (1 H, d, J=8.3 Hz), 7.44 (1 H, d, J=2.0 Hz), 7.34 (1 H, dd, J=2.0, 8.3 Hz), 6.37 (1 H, s), 3.72 (2 H, d, J=6.4 Hz), 2.57-2.49 (2 H, m), 2.39-2.31 (2 H, m), 1.92-1.80 (4 H, m), 1.43 (2 H, s), 0.77-0.69 (1 H, m), 0.58-0.54 (2 H, m), 0.11 (2 H, q, J=5.0 Hz)

Sources & evidence

ORD record
ord-91118e360886441d8de7b3cca67152bd
Source dataset
uspto-grants-2010_12
Patent number
US07851638B2

Reaction notes

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