Hydrochloric Acid → HCID 19092355, compound

HRID 487597Notes

Reaction equation

HRID 487597 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[CH2:4][CH2:3]1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[C:47]1([C:53]2[CH2:54][CH2:55][N:56]([CH2:59][CH2:60][CH2:61][CH2:62][NH2:63])[CH2:57][CH:58]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.Cl>O.C(N(CC)CC)C.CN(C)C=O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:63][CH2:62][CH2:61][CH2:60][CH2:59][N:56]3[CH2:55][CH:54]=[C:53]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:58][CH2:57]3)=[O:15])=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=2)[CH2:6][CH2:7]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 19092290HCID 19092290, compoundHCID 19092305HCID 19092305, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 19092355HCID 19092355, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred mixture of 4-(4-methylpiperazin-1-ylmethyl)-2-nitrobenzoic acid (0.28 g), hydroxybenzotriazole (0.14 g) and dry dimethylformamide (5 ml) was added dicyclohexylcarbodiimide (0.21 g), and the mixture was stirred for 1 hour at room temperature. Then 4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butylamine hydrochloride (0.27 g) and triethylamine (0.20 g) were added and the stirring was continued for additional 1 hour. 1N Hydrochloric acid (2 ml) and water (20 ml) were added and the mixture was washed with ethyl acetate, adjusted to pH 8 with aqueous sodium bicarbonate solution and extracted with ethyl acetate (x2). The combined organic extracts were dried over magnesium sulfate and solvent was evaporated to give 4-(4-methylpiprazin-1-ylmethyl)-2-nitro-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]benzamide (0.21).

Workup

  1. waitthe stirring was continued for additional 1 hour
  2. washthe mixture was washed with ethyl acetate
  3. extractionextracted with ethyl acetate (x2)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate and solvent
  5. customwas evaporated

Sources & evidence

ORD record
ord-cec77ddc3010475b9c748edd0a14ba7e
Source dataset
uspto-grants-1994_03
Patent number
US05296487

Reaction notes

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