Sodium Hydroxide → HCID 58909407, compound

HRID 1985076Notes

Reaction equation

HRID 1985076 reaction equation
Cl.[CH:2]([C:5]1[CH:6]=[C:7]([C:11]2([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:3].[OH-].[Na+].[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C@H:35]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:36]2[CH2:38][O:37]2)=[CH:30][C:29]=1[F:47])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[F:47][C:29]1[CH:30]=[C:31]([CH:32]=[CH:33][C:28]=1[O:27][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:34][C@H:35]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:43])[CH3:44])[C@H:36]([OH:37])[CH2:38][NH:17][C:11]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH:2]([CH3:4])[CH3:3])[CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 58909332HCID 58909332, compoundHCID 68423066HCID 68423066, compound

Product 1

HCID 58909407HCID 58909407, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The free base (270 mg, 1.24 mmol) of 1-(3-isopropylphenyl) cyclohexanamine hydrochloride 3 is obtained as a colorless oil by neutralization of the salt with 1N NaOH, extraction into ethyl acetate, drying over Na2SO4, and concentration. This is dissolved in 10 mL of CH2Cl2, and to it is added compound 17 (280 mg, 0.73 mmol) and 1.25 g of silica gel. The solvent is removed in vacuo and the reactants on silica are allowed to stand at ambient temperature for three days. The product mixture is eluted from the silica with 10% methanol in CH2Cl2, concentrated, and chromatographed on silica gel, eluting with 4% methanol (containing 2% NH4OH) in CH2Cl2, to afford compound 18 (238 mg, 0.39 mmol, 54%) as a colorless oil: 1H NMR (CDCl3) δ 7.43-7.26 (m, 8 H), 7.12 (m, 1 H), 6.94-6.84 (m, 3 H), 5.09 (s, 2 H), 4.64 (d, J=9 Hz, 1 H), 3.80 (br, 1 H), 3.31 (br, 1 H), 2.92-2.83 (m, 2 H), 2.7 (m, 1 H), 2.37 (m, 2 H), 2.0-1.95 (m, 4 H), 1.67-1.50 (m, 5 H), 1.35 (s+m, 10 H), 1.25 (d, J=7 Hz, 6 H).

Workup

  1. dry with materialdrying over Na2SO4, and concentration
  2. dissolutionThis is dissolved in 10 mL of CH2Cl2
  3. customThe solvent is removed in vacuo
  4. washThe product mixture is eluted from the silica with 10% methanol in CH2Cl2
  5. concentrationconcentrated
  6. customchromatographed on silica gel
  7. washeluting with 4% methanol (containing 2% NH4OH) in CH2Cl2

Sources & evidence

ORD record
ord-d4969f0c212c4282bc271df6c3266267
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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