Sodium Carbonate → HCID 14116911, compound

HRID 620273Notes

Reaction equation

HRID 620273 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH:20]([CH3:24])[C:21](=[O:23])[CH3:22])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+]>C(O)C>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH:20]([CH3:24])[CH:21]([OH:23])[CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 59692BatanoprideHCID 4311764Sodium borohydride

Product 1

HCID 14116911HCID 14116911, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-2-(2-butanon-3-yl)oxy-5-chloro-N-[2-(diethylamino)ethyl]benzamide (obtained by treating 1.2 g, 3.1 mmole, of the corresponding hydrochloride salt, prepared in Example 7C, with saturated sodium carbonate solution) and sodium borohydride (100 mg) in ethanol (20 ml) was heated under reflux for one hour. The solution was concentrated, diluted with water, acidified with 2N hydrochloride acid, and basified with saturated sodium carbonate solution. The mixture was extracted with methylene chloride to yield 1.16 g of foam. This material was chromatographed over deactivated silica using methylene chloride (100), methanol (2), ammonia (0.5) as the solvent system. The appropriate fractions were combined to yield the title compound (470 mg) as a foamy mixture of diastereoisomers. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.54 (bd, 1H); 8.2, 8.15 (2s, 1H); 6.32, 6.35 (2s, 1H); 4.36 (s, 2H); 4.24-4 (m, 1H); 4-2.12 (m, 3H); 2.8-2.52 (m, 6H); 1.41-0.96 (m, 12H).

Workup

  1. customobtained
  2. additionby treating 1.2 g, 3.1 mmole
  3. temperaturewas heated
  4. temperatureunder reflux for one hour
  5. concentrationThe solution was concentrated
  6. additiondiluted with water
  7. extractionThe mixture was extracted with methylene chloride

Sources & evidence

ORD record
ord-5455b50c235e4d8aa93b6e737aa4434a
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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