Sulfuric Acid → HCID 58930409, compound

HRID 908497Notes

Reaction equation

HRID 908497 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]CCOC2C=C(C=CC=2)C=O)[CH2:4][CH2:3]1.[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=2)[C:36]#[N:37])[CH2:24][CH2:23]1.[CH3:41]C(C[AlH]CC(C)C)C.OS(O)(=O)=O.[OH-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].[CH2:69]([Cl:71])Cl>C1(C)C=CC=CC=1.CO>[Cl:71][C:69]1[CH:3]=[CH:4][C:5]([C:6]2[N:37]=[C:36]([C:35]3[CH:34]=[C:33]([CH:40]=[CH:39][CH:38]=3)[O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH:25]3[CH2:24][CH2:23][N:22]([CH3:21])[CH2:27][CH2:26]3)[NH:2][C:7]=2[CH3:41])=[CH:8][CH:9]=1

Participants

10

Reactant 7

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 9855836Potassium sodium tartarateHCID 57434763HCID 57434763, compoundHCID 57434764HCID 57434764, compound

Product 1

HCID 58930409HCID 58930409, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

3-[4-(1-Methyl-piperidin-4-yl)-butoxy]-benzaldehyde. 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-5f352886fb974d4a84c7b85bf5e28b20
Source dataset
uspto-grants-2011_09
Patent number
US08017600B2

Reaction notes

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