Triethylamine → 4-acetylamino-5-chloro-2-methoxy-N-[4-(3-methylbutyl)-1-piperazinyl]benzamide

HRID 2286513Notes

Reaction equation

HRID 2286513 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([N:11]=O)[CH2:7][CH2:6]1.[C:14]([NH:17][C:18]1[C:26]([Cl:27])=[CH:25][C:21]([C:22](Cl)=[O:23])=[C:20]([O:28][CH3:29])[CH:19]=1)(=[O:16])[CH3:15].C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:14]([NH:17][C:18]1[C:26]([Cl:27])=[CH:25][C:21]([C:22]([NH:11][N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH:2]([CH3:13])[CH3:1])[CH2:6][CH2:7]2)=[O:23])=[C:20]([O:28][CH3:29])[CH:19]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 113799924-Acetamido-5-chloro-2-methoxybenzoyl chlorideHCID 234616511-(3-Methylbutyl)-4-nitrosopiperazine

Product 1

HCID 234616554-acetylamino-5-chloro-2-methoxy-N-[4-(3-methylbutyl)-1-piperazinyl]benzamideYield 56.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(3-methyl-butyl)-N'-nitroso-piperazine (2.5 g.) was added to 4-acetylamino-5-chloro-2-methoxy-benzoyl chloride (prepared from 3.5 g. of corresponding acid and thionylchloride) and triethylamine (5 ml.) in anhydrous toluene (250 ml.). After 1 hour, 10% sodium hydroxide (5 ml.) was added and the toluene layer separated, dried and evaporated to give 4-acetylamino-5-chloro-2-methoxy-N-[4-(3-methylbutyl)-1-piperazinyl]benzamide (3 g., 52%), m.p. 128°-30° (ex-ethylacetate/light petroleum.

Workup

  1. customthe toluene layer separated
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-f4484cc0a7684d558b20a8a8a1872326
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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