1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 70647876, compound

HRID 2202595Notes

Reaction equation

HRID 2202595 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29](O)=[O:30])[CH:24]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.O.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([C:29]([C:25]3[CH:24]=[C:23]([CH3:22])[CH:28]=[CH:27][N:26]=3)=[O:30])[CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628204-Methylpyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 10334132HCID 10334132, compound

Product 1

HCID 70647876HCID 70647876, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2.431 g of a known compound (±)-4-[(4-fluorophenyl)phenylmethoxy]piperidine, 974 mg of 4-methylpyridine-2-carboxylic acid, 2.922 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1.956 g of 1-hydroxybenzotriazole monohydrate, 29 mL of pyridine, and 208 mg of 4-dimethylaminopyridine was stirred for 1.8 hours. The mixture was poured into salt water and extracted with ethyl acetate twice. The extract was washed with a saturated saline solution and dried over magnesium sulfate. The solvent was distilled off, and then the residue was purified by silica gel column chromatography (chloroform/methanol (volume ratio)=20:1 to 15:1) to give the title compound (1.661 g (58%)).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe extract was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol (volume ratio)=20:1 to 15:1)

Sources & evidence

ORD record
ord-02d28e2175ec4627b8f9924ea50a2dce
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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