Water → HCID 22158462, compound

HRID 1073247Notes

Reaction equation

HRID 1073247 reaction equation
[CH:1]([C:4]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)([CH2:7][CH2:8][CH2:9]Cl)[C:5]#[N:6])([CH3:3])[CH3:2].CN[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:38][N:39](P(N(C)C)(N(C)C)=O)C>>[CH2:23]([CH2:38][NH:39][CH2:9][CH2:8][CH2:7][C:4]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=1)([CH:1]([CH3:3])[CH3:2])[C:5]#[N:6])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 11503N-MethylbenzeneethanamineHCID 12679HexamethylphosphoramideHCID 14245172HCID 14245172, compound

Product 1

HCID 22158462HCID 22158462, compoundYield 81%

Conditions

Temperature
80 °C

Procedure

29.5 g (0.1 mole) of α-isopropyl-α-(3-chloropropyl)-3,5-dimethoxyphenylacetonitrile and 13.5 g (0.1 mole) of N-methylphenethylamine were dissolved in 45 ml of hexamethylphosphorotriamide, and 30 g of powdered anhydrous potassium carbonate were added. The reaction mixture was heated at 80° C. for 4 hours and then cooled, after which 500 ml of water were added and the mixture was extracted twice with ether. The ether phase was washed several times with water and dried over potassium carbonate, and the ether was distilled off. The resulting base was converted to the hydrochloride. 34.8 g (81%) of a product of melting point 126°-127° C. were obtained.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted twice with ether
  3. washThe ether phase was washed several times with water
  4. dry with materialdried over potassium carbonate
  5. distillationthe ether was distilled off

Sources & evidence

ORD record
ord-dcb2f8853dfd422cb44a861f1093a57b
Source dataset
uspto-grants-1990_11
Patent number
US04968717

Reaction notes

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