Acetic Acid → HCID 18314284, compound

HRID 1419851Notes

Reaction equation

HRID 1419851 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(=O)(O)[O-].[Na+]>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:11][N:29]2[CH2:30][CH2:31][C:26]([OH:25])([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:27][CH2:28]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 963874-Phenylpiperidin-4-olHCID 5003444Sodium cyanoborohydrideHCID 18314251HCID 18314251, compound

Product 1

HCID 18314284HCID 18314284, compoundYield 138%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

3-(3,4-Dichlorophenyl)-4-(2-phenylimidazol-1-yl)butyraldehyde (1.0 g) in methanol (7 mL) was added to a solution of 4-hydroxy-4-phenylpiperidine (0.741 g) and acetic acid (0.24 mL) in methanol (7 mL). After 5 minutes, sodium cyanoborohydride (0.263 g) in methanol (7 mL) was added in a single portion. After being stirred for 2 hours, the reaction mixture was diluted with aqueous sodium bicarbonate, stirred for 30 minutes, and extracted with dichloromethane. The organic extracts were dried, evaporated, and chromatographed, with dichloromethane:methanol (gradient 98:2, 90:10) as eluent. The purified material was dissolved in dichloromethane, precipitated out as the hydrochloride salt with ethereal hydrogen chloride, evaporated, and placed under high vacuum overnight to give the title compound as a white solid (0.760 g); NMR: 7.92 (m,1), 7.69 (m,2), 7.59 (m,2), 7.50 (m,2), 7.36 (m,2), 7.28 (m,4), 7.10 (d,1, J=2.1), 6.85 (dd,1, J=2.1, 8.3), 4.70 (dd,1, J=4.5, 14.0), 4.57 (dd,1, J=10.5, 13.9), 3.47 (m,3), 3.27 (m,2), 3.14 (m,1), 2.84 (m,1), 2.47-2.20 (m,4), 1.93 (m,2); MS: m/z=520(M+1) Analysis for C30H31Cl2N3O.02.80 HCl.0.15 Et2O: Calculated: C, 58.00; H, 5.61; N, 6.63; Found: C, 57.99; H, 5.80; N, 6.77.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated
  5. customchromatographed, with dichloromethane
  6. dissolutionThe purified material was dissolved in dichloromethane
  7. customprecipitated out as the hydrochloride salt with ethereal hydrogen chloride
  8. customevaporated
  9. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-b98454f7d2944b24b5ac26da5a204a20
Source dataset
uspto-grants-1999_03
Patent number
US05889024

Reaction notes

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