Hydrochloric Acid → HCID 14624180, compound

HRID 1460469Notes

Reaction equation

HRID 1460469 reaction equation
[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].Cl.[CH:29](Cl)(Cl)[Cl:30]>C(O)(=O)C>[ClH:30].[CH3:1][N:2]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH2:3][CH2:4][CH2:5][N:6]1[C:7](=[O:15])[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[O:10][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14624217HCID 14624217, compound

Product 1

HCID 14624180HCID 14624180, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2 g (5.37 mmol) of N-{3-[(methyl)(3,4-dimethoxyphenethyl)amino]propyl}salicylamide in 18 ml of chloroform and 1 ml of acetic acid is treated for 2 min with a stream of gaseous hydrochloric acid. 340 milligrams of trioxymethylene are then added to the above mixture, which is heated for 20 min to 70°-75° C. After return to room temperature, a stream of nitrogen is passed through for 30 min and the mixture is then filtered on a sinter and evaporated to dryness. The residue is taken up in toluene and re-evaporated to dryness in a rotary evaporator under vacuum. The solid residue (3.10 g) is ground in isopropyl ether and filtered. The cream powder obtained (m=2.1 g) is recrystallized in a 75:25 i-PrOH/EtOH mixture to give 1.53 g (yld=68%) of compound A of formula: ##STR6##

Workup

  1. addition340 milligrams of trioxymethylene are then added to the above mixture, which
  2. temperatureis heated for 20 min to 70°-75° C
  3. customto room temperature
  4. customis passed through for 30 min
  5. filtrationthe mixture is then filtered on a sinter
  6. customevaporated to dryness
  7. customre-evaporated to dryness in a rotary evaporator under vacuum
  8. filtrationfiltered
  9. customThe cream powder obtained (m=2.1 g)
  10. customis recrystallized in a 75:25 i-PrOH/EtOH mixture

Sources & evidence

ORD record
ord-efaea55f22e6469eada7fef9dae6f354
Source dataset
uspto-grants-1991_12
Patent number
US05071850

Reaction notes

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