Triethylamine → Tert-butyl 3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]propylcarbamate

HRID 915542Notes

Reaction equation

HRID 915542 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.Br[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 11188863Tert-butyl 3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]propylcarbamateYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3,4-Dichlorophenoxy)piperidine (10 g) was dissolved in N,N-dimethylformamide (DMF; 50 ml) and triethylamine (14.8 ml) was added. 1,1-Dimethylethyl (3-bromopropyl)-carbamate (10 g) was added and the solution was stirred at room temperature for 24 hrs. The solvent was evaporated and the resulting solid was dissolved in ethyl acetate and water was added, the organic phase was separated, dried with MgSO4 and evaporated to give the subtitle compound as a solid (17.51 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting solid was dissolved in ethyl acetate
  3. additionwater was added
  4. customthe organic phase was separated
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-f97276ee935c416a873c03e3c95520e2
Source dataset
uspto-grants-2007_09
Patent number
US07265227B2

Reaction notes

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