Water → HCID 25226975, compound

HRID 1894856Notes

Reaction equation

HRID 1894856 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[C:14]1([N:20]2[C:24]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:23][N:22]([CH2:30][C:31](O)=[O:32])[CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)CCCN=C=NCC.O>ClCCl>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:31](=[O:32])[CH2:30][N:22]1[CH2:23][C:24]2([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[N:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:21]1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 68629874HCID 68629874, compound

Product 1

HCID 25226975HCID 25226975, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

130 μl (0.69 mmol) of 2,6-diisopropylaniline are added to a solution of 180 mg (0.65 mmol) of (1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)acetic acid in 20 ml of dichloromethane. The solution is cooled to −10° C. and 132 mg (0.69 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide are added. The medium is allowed to return to room temperature and stirred for 4 h and then at reflux for one day and again at room temperature for 5 days. The medium is then poured into water and extracted with dichloromethane. The organic phases are collected and washed with water. They are dried over sodium sulfate. The solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 90/10, v/v). 25 mg of N-(2,6-diisopropylphenyl)-2-(1-phenyl-1,3-diazaspiro[4.5]dec-3-yl)acetamide are obtained in the form of a white solid. M.p. 151-3° C., yield=8.8%.

Workup

  1. customto return to room temperature
  2. temperatureat reflux for one day and again at room temperature for 5 days
  3. extractionextracted with dichloromethane
  4. customThe organic phases are collected
  5. washwashed with water
  6. dry with materialThey are dried over sodium sulfate
  7. customThe solvents are evaporated
  8. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 90/10

Sources & evidence

ORD record
ord-dd96d546efd5427fa53e2a091ec1ada1
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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