Dimethylformamide → HCID 57009198, compound

HRID 1085788Notes

Reaction equation

HRID 1085788 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 8090° C. was added dropwise over 1 h freshly distilled bromoacetaldehyde diethylacetal (4.50 g, 22.5 mmol, Aldrich Co.). After 13 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 1 N NaOH (200 ml), extracted twice with CH2C12 (total of 100 ml), and dried (MgS04). 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: 1H NMR (CDCl3) ≃1.10 (t, 3), 1.12 (t, 3 ), 1.70 (bs, 1), 2.50 (dd, 1), 2.58 (dd, 1) 2.91 (dd, 1), 2.98 (dd, 1), 3.39 (1), 3.59 (dt, 1), 3.86 (dd, 1) 4.53 (dd, 1) 7.16-7.40 (m, 10); 13C NMR (CDCl3) δ15.5 (q), 45.5 (t), 50.0 (t), 62.0 (t), 62.2 (t), 64.9 (d), 102.0 (d), 126.5, 127.3, 128.5, 129.5 (all d), 139.0, 143.8 (all s).

Workup

  1. customN-(2,2-diethoxyethyl)-diphenylethylamine was prepared
  2. waitAfter 13 h
  3. extractionextracted twice with CH2C12 (total of 100 ml)
  4. customdried (MgS04)
  5. customThe solvent was evaporated
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-69fdf4c9134e484eaf6f4a23996667c0
Source dataset
uspto-grants-1991_04
Patent number
US05011834

Reaction notes

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