Hydrochloric Acid → HCID 53695102, compound

HRID 1743466Notes

Reaction equation

HRID 1743466 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:40])[C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)[C:19]([O:29]COC)=[C:18]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=3)[CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1COCC1.CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)[C:19]([OH:29])=[C:18]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=3)[CH:17]=2)=[O:40])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 22237522HCID 22237522, compound

Product 1

HCID 53695102HCID 53695102, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-7-phenylheptyl-3,5-bis-(3-methylphenyl)-4-methoxymethoxybenzamide (1.04 g, 1.94 mmol) in 3.5 mL THF was added 2N HCl (1.1 mL, 2.2 mmol) at room temperature and the reaction mixture was refluxed for 2 hours before a catalytic amount of camphorsulfonic acid was added. The reaction was refluxed overnight and the resulting goo was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. This yielded an oil that was passed through a pad of silica gel using 20% EtOAc: 80% Hexanes. There yielded 730 mg, 81% of a light yellow viscous oil. 1H NMR (CDCl3) δ 1.33–1.39 (m, 6H); 1.59–1.63 (m, 6H); 2.42 (s, 6H); 2.58 (t, J=7.69 Hz, 2H); 3.44 (quartet, J=7.03 Hz, 2H); 6.06 (t, J=7.50 Hz, 1H); 7.14–7.18 (m, 3H); 7.22–7.28 (m, 4H); 7.34–7.40 (m, 6H); 7.68 (s, 2H); IR 3525, 3025, 2925, 2850, 1630, 1600, 1530, 1460, 1325, 1230, and 700 cm−1; mass spectrum [(+)ESI], m/z 492 [M+H]+; Anal Calcd. For C34H37NO2: C, 83.06; H, 7.59; N, 2.85. Found: C, 83.80; H, 7.62; N, 2.93.

Workup

  1. additionwas added
  2. temperatureThe reaction was refluxed overnight
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThis yielded an oil that

Sources & evidence

ORD record
ord-20cf3cd0c2444f8390929654ae6a8e93
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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