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

HRID 1086031Notes

Reaction equation

HRID 1086031 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-0bab98f4aac446c082538a76859e8e06
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

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