Hydrochloric Acid → HCID 10299954, compound

HRID 1182082Notes

Reaction equation

HRID 1182082 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27].Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.O.C(Cl)(Cl)Cl>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:33](=[O:34])[C:32]2[CH:31]=[CH:30][C:29]([N+:26]([O-:28])=[O:27])=[CH:37][CH:36]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 61084-Nitrobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11279224HCID 11279224, compound

Product 1

HCID 10299954HCID 10299954, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 4 mL of chloroform was added 4-[4-benzhydryloxy]piperidino]-1-butanol obtained from step 2 (0.11 g), 4-nitrobenzoic acid (0.1 g), 4-dimethylaminopyridine (DMAP, 0.12 g), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodimide hydrochloride (0.1 g). The resulting mixture was allowed to react at room temperature for 3 hrs. before adding water to end the reaction. The resulting solution was acidified with 1N hydrochloric acid, and extracted by using chloroform. An organic solution layer was washed with 1N sodium hydroxide, dehydrated over magnesium sulfate, filtered, and concentrated under reduced pressure. The column chromatography was performed thereon, thereby obtaining crude yellowish liquid product (0. 12 g, 76% yield) of the title.

Workup

  1. customto react at room temperature for 3 hrs
  2. customthe reaction
  3. extractionextracted
  4. washAn organic solution layer was washed with 1N sodium hydroxide
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customobtaining crude yellowish liquid product (0. 12 g, 76% yield) of the title

Sources & evidence

ORD record
ord-5c8b2e09977a4f8bb8b7569e7235a66a
Source dataset
uspto-grants-2007_10
Patent number
US07288552B2

Reaction notes

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