Water → N-((6-(2-((cyclohexylamino)methyl)phenyl)pyridin-2-yl)(2-isopropylphenyl)methyl)-2,6-diisopropylaniline

HRID 629854Notes

Reaction equation

HRID 629854 reaction equation
[CH:1]1([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:20]=[C:19]([CH:21]=[N:22][C:23]3[C:28]([CH:29]([CH3:31])[CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=3[CH:32]([CH3:34])[CH3:33])[CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[Li])([CH3:37])[CH3:36].O>CCOCC>[CH:1]1([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:20]=[C:19]([CH:21]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[CH:35]([CH3:37])[CH3:36])[NH:22][C:23]3[C:24]([CH:32]([CH3:34])[CH3:33])=[CH:25][CH:26]=[CH:27][C:28]=3[CH:29]([CH3:30])[CH3:31])[CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 118340994N-((6-(2-((cyclohexylamino)methyl)phenyl)pyridin-2-yl)methylene)-2,6-diisopropylanilineHCID 178506681HCID 178506681, compound

Product 1

HCID 118340995N-((6-(2-((cyclohexylamino)methyl)phenyl)pyridin-2-yl)(2-isopropylphenyl)methyl)-2,6-diisopropylaniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Et2O (10 mL) was added to compound 9 (0.189 g, 0.417 mmol) to form a clear pale yellow solution. At −80° C., an Et2O (5 mL) solution of 2-isopropylphenyllithium (0.136 g, 1.08 mmol) was added dropwise to form a red-purple solution. The mixture was allowed to slowly warm to ambient temperature overnight. Water (50 mL) was then added followed by Et2O (50 mL). The organics were separated, dried with brine and then MgSO4. Evaporation of the volatiles afforded compound 10, which did not require any purification. Yield: 0.224 g, 76.2%. 1H NMR (CD2Cl2): δ 7.67 (t, 2H), 7.1-7.53 (m, 10H), 7.00 (m, 3H), 5.44 (d, 1H), 4.40 (d, 1H), 3.69 (s, 2H), 3.11 (sept, 1H), 2.91 (sept, 2H), 2.24 (m, 1H), 1.5-1.7 (m, 6H), 1.25 (d, 3H), 1.1-1.2 (m, 4H), 0.97 (d, 12H), 0.93 (d, 6H).

Workup

  1. customto form a clear pale yellow solution
  2. customto form a red-purple solution
  3. customThe organics were separated
  4. dry with materialdried with brine
  5. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-27070a9a0cf14a67af7dcca788e4c8d0
Source dataset
uspto-grants-2016_04
Patent number
US09315526B2

Reaction notes

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