Water → N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-methoxybenzamide hydrochloride

HRID 496874Notes

Reaction equation

HRID 496874 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](Cl)=[O:39].O>ClCCl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][NH:21][C:38](=[O:39])[C:37]2[CH:41]=[CH:42][CH:43]=[C:35]([O:34][CH3:33])[CH:36]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 223224532-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate

Product 1

HCID 22322410N-{2-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethyl}-3-methoxybenzamide hydrochlorideYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 1 step (iv) (2.0 g) was dissolved in dichloromethane (490 ml), triethylamine (1.85 ml) and 3-methoxybenzoyl chloride (0.66 g) were added. After 72 hours at room temperature, water was added, the organic phase separated, dried and concentrated to a gum. The product was dissolved in dichloromethane and treated with 1.0M ethereal hydrogen chloride solution to give the titled product as a solid (0.88 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated to a gum
  4. dissolutionThe product was dissolved in dichloromethane
  5. additiontreated with 1.0M ethereal hydrogen chloride solution

Sources & evidence

ORD record
ord-a8a4825015344bb386d7bfd414979f6b
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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