4-Cyanophenol → HCID 178456380, compound

HRID 1984033Notes

Reaction equation

HRID 1984033 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:19]([C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)#[N:20].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:18][C@H:15]2[CH2:14][CH2:13][C@H:12]([C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]3)=[O:11])[CH2:17][CH2:16]2)=[CH:23][CH:22]=1)#[N:20]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 97268Di-tert-butyl azodicarboxylateHCID 178456387HCID 178456387, compound

Product 1

HCID 178456380HCID 178456380, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.0 g (3.93 mmol) of cis-(4-isopropyl-piperazin-1-yl)-(4-hydroxy-cyclohexyl)-methanone, 0.515 g (4.3 mmol) of 4-cyanophenol, 1.28 g (4.88 mmol) of triphenylphisphine in 6 ml THF, 1.11 g (4.82 mmol) of di-tert-butyl azodicarboxylate in 6 ml of THF was added at 0° C., and stirred for 72 hr at room temperature. After evaporation, the residue was purified by column chromatography on silica gel eluting with cyclohexane and ethyl acetate=from 1:1 to 1:3, then dichloromethane and methanol=19:1. The combined product fractions were evaporated to dryness to yield 0.26 g (19% yields) of the titled compound. MS (m/e): 356.2 (MH+).

Workup

  1. customAfter evaporation
  2. customthe residue was purified by column chromatography on silica gel eluting with cyclohexane and ethyl acetate=from 1:1 to 1:3
  3. customThe combined product fractions were evaporated to dryness
  4. customto yield

Sources & evidence

ORD record
ord-e5f28192823648eb9f4975bb5c2d4aa7
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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