Ethyl 3-(7-amidino-2-naphthyl)-2-[4-[(4-piperidinyl)methoxy]phenyl]propionate dihydrochloride → 3-(7-Amidino-2-naphthyl)-2-[4-[(4-piperidinyl)methoxy]phenyl]propionic Acid Hydrochloride Monohydrate

HRID 361935Notes

Reaction equation

HRID 361935 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][CH:17]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:25][CH:24]=3)[C:18]([O:20]CC)=[O:19])=[CH:13]2)=[CH:8][CH:7]=1)(=[NH:5])[NH2:4]>Cl>[OH2:19].[ClH:1].[C:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][CH:17]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:25][CH:24]=3)[C:18]([OH:20])=[O:19])=[CH:13]2)=[CH:8][CH:7]=1)(=[NH:4])[NH2:5]

Participants

3

Reactant 1

HCID 21844349Ethyl 3-(7-amidino-2-naphthyl)-2-[4-[(4-piperidinyl)methoxy]phenyl]propionate dihydrochloride

Product 1

HCID 700745613-(7-Amidino-2-naphthyl)-2-[4-[(4-piperidinyl)methoxy]phenyl]propionic Acid Hydrochloride MonohydrateYield 114.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1.51 g of ethyl 3-(7-amidino-2-naphthyl)-2-[4-[(4-piperidinyl)methoxy]phenyl]propionate dihydrochloride was dissolved in 50 ml of concentrated hydrochloric acid, and the solution was allowed to stand still in a sealed container at room temperature for 62 hours. After drying the resulting reaction solution under a reduced pressure, the thus obtained residue was purified by applying it to a column packed with a highly porous polymer type synthetic adsorbent (styrene-divinylbenzene polymer: HP-20). Thereafter, the thus eluted fractions of interest were pooled, and mixed with a small amount of ethanol, and then the crystals thus precipitated were collected by filtration. In this way, 0.79 g of the title compound was obtained in the form of crystals.

Workup

  1. customAfter drying
  2. customthe resulting reaction solution under a reduced pressure
  3. customthe thus obtained residue was purified
  4. additionmixed with a small amount of ethanol
  5. customthe crystals thus precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c712fdccd8e94cf18d5c2291112ffabd
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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