Dimethylformamide → HCID 57009198, compound

HRID 2293961Notes

Reaction equation

HRID 2293961 reaction equation
[C:1]1([CH:7](N)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3]C=1.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].C(=O)([O-])[O-].[K+].[K+].[CH3:31][N:32](C)C=O>[OH-].[Na+]>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH:32][CH2:31][CH:8]([C:7]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 264821,2-DiphenylethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 57009198HCID 57009198, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

N-(2,2-diethoxyethyl)-diphenylethylamine was prepared according to the procedure of Takayama, H., Chem. Lett. 865 (1978). To a stirred solution of 1,2-diphenylethylamine (3.94 g, 20.0 mmol, Aldrich Co., used as received) in N,N-dimethylformamide (DMF) (10 ml) at 80°-90° C. was added dropwise over 1 h freshly distilled bromoacetaldehyde diethylacetal (4.50 g, 22.5 mmol, Aldrich Co.). After 1 h, potassium carbonate (2.76 g, 20.0 mmol) was added. After 13 h, the brown mixture was cooled to 25° C. and then the mixture was diluted with 1N NaOH (200 ml), extracted twice with CH2Cl2 (total of 100 ml), and dried (MgSO4). The solvent was evaporated and the residue was distilled to give N-(2,2-diethoxyethyl)-diphenylethylamine (5.29 g, 84%): bp 150°-160° C./0.50 mm;

Workup

  1. customN-(2,2-diethoxyethyl)-diphenylethylamine was prepared
  2. waitAfter 13 h
  3. extractionextracted twice with CH2Cl2 (total of 100 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-1b9083f8d24846df985a3930a3c724ad
Source dataset
uspto-grants-1997_11
Patent number
US05688789

Reaction notes

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