Sulfuric Acid → HCID 57434764, compound

HRID 2420979Notes

Reaction equation

HRID 2420979 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#N)[CH2:4][CH2:3]1.CC(C[AlH]CC(C)C)C.[OH:30]S(O)(=O)=O.[OH-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:30])[CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 9855836Potassium sodium tartarateHCID 57434763HCID 57434763, compound

Product 1

HCID 57434764HCID 57434764, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[4-(1-methyl-piperidin-4-yl)-butoxy]-benzonitrile (0.84 g, 3.09 mmol) in toluene (5 mL) at 0° C. was added 1.5 M DIBAL-H in toluene (4.63 mL, 4.63 mmol). After 3 h, methanol (9 mL) and 1.0 M H2SO4 (10 mL) were added dropwise. After stirring for 30 min, the solution was neutralized with 1.0 M sodium hydroxide (10 mL) followed by addition of satd. aq. sodium potassium tartrate (40 mL) and CH2Cl2 (100 mL). After stirring for 30 min the solution was extracted with CHCl3 (3×50 mL), washed with brine and dried over Na2SO4. Purification by Method 1 afforded 0.56 g (66%) of the title compound. 1H NMR (400 MHz, CDCl3): 9.97 (s, 1H), 7.46-7.43 (m, 2H), 7.39-7.37 (m, 1H), 7.19-7.15 (m, 1H), 4.02 (t, J=6.6, 2H), 2.86-2.80 (m, 2H), 2.25 (s, 3H), 1.92-1.83 (m, 2H), 1.83-1.75 (m, 2H), 1.73-1.63 (m, 2H), 1.54-1.44 (m, 2H), 1.34-1.18 (m, 5H).

Workup

  1. additionfollowed by addition of satd
  2. stirringAfter stirring for 30 min the solution
  3. extractionwas extracted with CHCl3 (3×50 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customPurification by Method 1

Sources & evidence

ORD record
ord-43f4d930bc2e41ec9c9785b9952568ad
Source dataset
uspto-grants-2011_06
Patent number
US07956066B2

Reaction notes

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