Sodium Hydroxide → HCID 14326696, compound

HRID 622781Notes

Reaction equation

HRID 622781 reaction equation
C([NH:6][C:7]1[C:8](=[O:31])[NH:9][C:10]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:19]=2)=[N:11][CH:12]=1)(OCC)=O.[OH-].[Na+]>C(O)(=O)C>[NH2:6][C:7]1[C:8](=[O:31])[NH:9][C:10]([NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:19]=2)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14326694HCID 14326694, compound

Product 1

HCID 14326696HCID 14326696, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-carbethoxyamino-2-[3-(3-piperidinomethylphenoxy)propylamino]-4(3H)-pyrimidone (1.70 g; 3.96 mmoles) in 11.3 ml (28.3 meq.) of 10% aqueous NaOH was heated at an oil bath temperature of 120° C. for 20 minutes. The reaction mixture was neutralized with acetic acid and evaporated under reduced pressure. The residue was placed on 250 g of silica gel (230-400 mesh) and chromatographed by flash chromatography using CH2Cl2 /CH3OH/NH4OH (80:20:1) as the eluent. The appropriate fractions containing product were combined, evaporated and treated wih ethanolic hydrochloric acid, and then diluted with ether to give 0.28 g of the title compound as its hydrochloride salt. The NMR spectrum (100 MHz) in d6 dimethyl sulfoxide gave the following resonances δ: 7.14 (m, 4H); 6.94 (s, 1H); 4.0 (m, 4H); 3.32 (t, 2H); 2.84 (m, 4H); 1.94 (m, 2H); 1.66 (m, 6H).

Workup

  1. customevaporated under reduced pressure
  2. customchromatographed by flash chromatography
  3. additionThe appropriate fractions containing product
  4. customevaporated
  5. additiontreated wih ethanolic hydrochloric acid
  6. additiondiluted with ether

Sources & evidence

ORD record
ord-87917c6cf4714abdaab7960fdbf001b1
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

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