Triethylamine → N-7-Phenylheptyl-3,5-bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzamide

HRID 324091Notes

Reaction equation

HRID 324091 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[CH:17]=[C:18]([C:23]2[CH:24]=[C:25]([CH:29]=[C:30]([C:36]3[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=3)[C:31]=2[O:32][CH2:33][O:34][CH3:35])[C:26](O)=[O:27])[CH:19]=[C:20]([CH3:22])[CH:21]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O.O.C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:26](=[O:27])[C:25]2[CH:29]=[C:30]([C:36]3[CH:37]=[C:38]([CH3:43])[CH:39]=[C:40]([CH3:42])[CH:41]=3)[C:31]([O:32][CH2:33][O:34][CH3:35])=[C:23]([C:18]3[CH:17]=[C:16]([CH3:15])[CH:21]=[C:20]([CH3:22])[CH:19]=3)[CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 64319907-Phenylheptan-1-amineHCID 222375543,5-Bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzoic acid

Product 1

HCID 22237438N-7-Phenylheptyl-3,5-bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzamideYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A flamed dried round bottom flask was charged with 7-phenylheptyl amine (354 mg, 2.78 mmol) and 20 mL anhydrous CH2Cl2. To this solution was added 3,5-bis-(3,5-dimethylphenyl)-4-methoxymethoxybenzoic acid (780 mg, 1.85 mmol), triethyl amine (563 mg, 5.56 mmol, 726 μL), anhydrous 1-hydroxybenzotriazole (275 mg, 2.04 mmol), and DCC (459 mg, 2.22 mmol), all at room temperature. The reaction mixture was stirred at room temperature for one-half hour. Then the reaction was worked up by adding water then extracting with EtOAc (3×). The combined organic extracts were dried over Na2SO4 and the solvent removed in vacuo to give a semisolid to which CH2Cl2 was added. This suspension was subjected to column chromatography (15% EtOAc:85% Hexanes) to give 600 mg, 54.5% of the amide as a colorless oil. 1H NMR (CDCl3) δ1.34 (bs, 6H); 1.57 (m, 4H); 2.36 (s, 12H); 2.572 (t, J=8.18 Hz, 2H); 2.681 (s, 3H); 3.414 (quartet, J=8.18 Hz, 2H); 4.39 (s, 2H); 6.04 (t, J=5.73 Hz, 1H); 6.97 (s, 2H); 7.12-7.27 (m, 9H); 7.67 (s, 2H).

Workup

  1. customA flamed dried round bottom flask
  2. customat room temperature
  3. extractionthen extracting with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customto give a semisolid to which CH2Cl2
  7. additionwas added

Sources & evidence

ORD record
ord-36d0d4451b074d8a8cabdbd2da347a13
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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