Hydrochloric Acid → 2-Amino-N-[4-[2-(dimethylamino)ethoxy]benzyl]benzamide

HRID 703534Notes

Reaction equation

HRID 703534 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.[C:15]12[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=1)[NH:20]C(=O)O[C:16]2=[O:17].Cl>C(OCC)(=O)C>[NH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=1[C:16]([NH:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:14])[CH3:1])=[CH:7][CH:8]=1)=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamine

Product 1

HCID 151369722-Amino-N-[4-[2-(dimethylamino)ethoxy]benzyl]benzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.00 g of 4-[2-(dimethylamino)ethoxy]benzylamine in 20 ml of ethyl acetate was added 1.04 g of isatoic anhydride. The mixture was stirred at room temperature for 15 minutes. Hydrochloric acid (10%) was added to the mixture. The aqueous layer was separated, made alkaline with potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. Recrystallization of the residue from ethyl acetate gave 1.85 g of colorless pillars, m.p. 104°-105° C.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customRecrystallization of the residue from ethyl acetate
  7. customgave 1.85 g of colorless pillars, m.p. 104°-105° C.

Sources & evidence

ORD record
ord-007bd925901c4ee7bc891d47acbbd44f
Source dataset
uspto-grants-1991_01
Patent number
US04983633

Reaction notes

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