Methyl anisate → 1-{[4-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thien-2-yl]carbonyl}-4-phenylpiperidine-4-carboxamide

HRID 1958681Notes

Reaction equation

HRID 1958681 reaction equation
ClC1C=C(Cl)C=CC=1CC(O)=O.COC1C=CC(C(OC)=O)=CC=1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:33]1[CH:34]=[C:35]([C:46](O)=[O:47])[S:36][C:37]=1[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1.[C:49]1([C:55]2([C:61]([NH2:63])=[O:62])[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CCN(CC)CC>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:33]1[CH:34]=[C:35]([C:46]([N:58]2[CH2:57][CH2:56][C:55]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)([C:61]([NH2:63])=[O:62])[CH2:60][CH2:59]2)=[O:47])[S:36][C:37]=1[C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1

Participants

8

Reactant 5

HCID 8499Methyl anisateHCID 882092,4-Dichlorophenylacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30171304-Phenylpiperidine-4-carboxamideHCID 672995574-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid

Product 1

HCID 671846951-{[4-(2,4-Dichlorophenyl)-5-(4-methoxyphenyl)thien-2-yl]carbonyl}-4-phenylpiperidine-4-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-(2,4-dichlorophenyl)-5-(4-methoxyphenyethiophene-2-carboxylic acid is prepared, according to the procedure used in stages 1A)-1E), from (2,4-dichlorophenyl)acetic acid and methyl 4-methoxybenzoate. 3.8 g of 4-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid, 2.53 g of 4-phenylpiperidine-4-carboxamide (preparation 2), 0.72 ml of Et3N and 3.53 g of TBTU are added at AT to 100 ml of CH2Cl2. The mixture is stirred overnight. It is evaporated to dryness, water is added and the compound obtained is extracted with ethyl acetate. The organic phase is dried and evaporated to dryness. After crystallizing, washing with ethyl ether, filtering and then drying, 5.1 g of the expected compound are obtained.

Workup

  1. customIt is evaporated to dryness, water
  2. additionis added
  3. customthe compound obtained
  4. extractionis extracted with ethyl acetate
  5. customThe organic phase is dried
  6. customevaporated to dryness
  7. customAfter crystallizing
  8. washwashing with ethyl ether
  9. filtrationfiltering
  10. customdrying

Sources & evidence

ORD record
ord-525a0613b454439f994e88bda75255e6
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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