Ammonium Hydroxide → HCID 22475634, compound

HRID 2184090Notes

Reaction equation

HRID 2184090 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1.C[Si]([C:36]#[N:37])(C)C.[NH4+].[OH-]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:31])([C:23]([F:24])([F:25])[F:26])[C:27]([F:28])([F:29])[F:30])=[CH:20][CH:21]=2)([C:36]#[N:37])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14923Ammonium Hydroxide2×HCID 192201-Benzyl-4-piperidoneHCID 82115Trimethylsilyl cyanideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 22475634HCID 22475634, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-benzyl-4-piperidone (1.3 mL, 7.0 mmol) and 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Oakwood, 2.0 g, 7.7 mmol) in glacial acetic acid (6.6 mL) was added trimethylsilyl cyanide (0.9 mL, 7.0 mmol) over 5 minutes. After 30 minutes, the reaction was poured in to a mixture of ice (6.5 g) and NH4OH (6.5 mL). Additional NH4OH was added until pH=10. The product was extracted with CH2Cl2 (3×), then washed with brine, dried (Na2SO4), and concentrated to afford the title compound as an off-white solid (3.4 g, quantitative yield). MS (ES+) m/z 458 (MH+).

Workup

  1. extractionThe product was extracted with CH2Cl2 (3×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6df30c0ad69c4a36a113b8a1382df1ae
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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