Water → HCID 90015922, compound

HRID 591149Notes

Reaction equation

HRID 591149 reaction equation
[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:24][NH:25][CH3:26].C[Si](Cl)(C)C.O>ClCCl>[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:25]([CH3:26])[CH3:24])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 10473Dimethylamine, hydrochlorideHCID 10109258Benzoyl chloride, 4-[3-(dibutylaMino)propoxy]-

Product 1

HCID 90015922HCID 90015922, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6.5 g of 4-(3-dibutylaminopropoxyl)benzoyl chloride (V) (0.02 mol) is dissolved in 60 mL of dichloromethane. 1.63 g of dimethylamine HCl (0.02 mol, 1 eq) is added and the reaction mixture is cooled to 0° C. 0.43 g TMSCl (0.004 mol, 0.2 eq) is added in 5 min. The reaction mixture is heated to room temperature and stirred for 5 hours. 50 mL of water is added to the mixture, it is stirred for 15 min and the phases are separated. The organic phase is washed with 30 mL of water then it is concentrated. The residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1) to give 4.68 g of the title compound (VIb) (70%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture is heated to room temperature
  2. stirringis stirred for 15 min
  3. customthe phases are separated
  4. washThe organic phase is washed with 30 mL of water
  5. concentrationit is concentrated
  6. customThe residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1)

Sources & evidence

ORD record
ord-aa868a42e32c404b90084e4c9333d37d
Source dataset
uspto-grants-2016_01
Patent number
US09238636B2

Reaction notes

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