Triethylamine → tert-Butyl 2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethylcarbamate

HRID 1059009Notes

Reaction equation

HRID 1059009 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][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C(OCC)(=O)C>CN(C=O)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][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 22322299tert-Butyl 2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethylcarbamateYield 76.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

The product from step (ii) (6.55 g) was dissolved in DMF (50 ml) and triethylamine (7.9 ml) was added. tert-Butyl 2-bromoethylcarbamate (4.3 g) in DMF (5 ml) was added and the solution stirred at room temperature for 3 days. Ethyl acetate and water were added, the organic phase separated, dried and evaporated to a gum. Purification by chromatography (dichloromethane:methanol 95:5) gave the sub-titled product as a gum (5.7 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. customevaporated to a gum
  4. customPurification by chromatography (dichloromethane:methanol 95:5)

Sources & evidence

ORD record
ord-de73112e418d4a6490224780d1c8f878
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

Loading…