Triethylamine → N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide

HRID 2395043

Reaction equation

HRID 2395043 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.Cl.[CH3:43][NH:44][OH:45].CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[CH3:43][N:44]([OH:45])[C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 77906N-methylhydroxylamine hydrochlorideHCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

Product 1

HCID 18973882N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamideYield 36.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-(2-benzyloxyphenyl)propyl]benzoic acid (1.0 g), 1-HOBT (0.39 g) and DCCI (0.595 g) in DMF (10 ml) was stirred for 3 hours, then added to a solution of N-methylhydroxylamine HCl (0.24 g) and Et3N (0.29 g) in CH2Cl2 (10 ml) and stirred for 70 hours. The product was extracted in 2N aqueous KOH and washed with ethyl acetate. The aqueous solution was acidified with concentrated HCl and extracted with diethyl ether. The solvent was evaporated and the residue subjected to flash chromatography on silica gel (using diethyl ether:methanol (95:5) as eluant) to give N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide as a gum (0.39 g).

Workup

  1. stirringstirred for 70 hours
  2. extractionThe product was extracted in 2N aqueous KOH
  3. washwashed with ethyl acetate
  4. extractionextracted with diethyl ether
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5bfdfe74464e4b01b0b7df5c5b5d7ece
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Linked notes

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