Hydrochloric Acid → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-hydroxy-propoxy)-benzamide

HRID 620256Notes

Reaction equation

HRID 620256 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][CH2:20][C:21](=[O:23])[CH3:22])[CH:3]=1.[BH4-].[Na+].Cl>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][CH2:20][CH:21]([OH:23])[CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 141168894-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-propoxy)-benzamide

Product 1

HCID 141169084-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-hydroxy-propoxy)-benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-propanon-1-yl)oxybenzamide (1.28 g, 3.7 mmoles) and sodium borohydride (80 mg, 2.1 mmoles) in absolute ethanol (15 ml) was refluxed for 30 minutes, followed by addition of another 50 mg (1.3 mmole) of sodium borohydride and reflux for 10 minutes. The mixture was acidified with 2N HCl and concentrated in vacuo. The residue was partitioned between water and ether, and the ether layer was discarded. The aqueous layer was made basic with Na2CO3 and the solid filtered off to give 0.80 g (77%) of the title compound mp 149°-150°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.48 (bs, 1H); 8.16 (s, 1H); 6.28 (s, 1H); 4.4-3.4 (m, 7H); 2.64 (m, 6H); 1.26 (d, J=7.5 Hz, 3H); 1.08 (t, 3H).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturereflux for 10 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and ether
  5. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-a4c20d121b3844008f36c9e4b6eb6552
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

Loading…