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

HRID 968759

Reaction equation

HRID 968759 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)C.O>CN(C=O)C>[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

6

Reactant 4

HCID 8471TriethylamineHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 21584184Diethylether water

Product 1

HCID 22322299tert-Butyl 2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethylcarbamateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1 Step (b) (8.6 g) was dissolved in DMF (60 ml) and triethylamine (12 ml) was added. tert-Butyl 2-bromoethylcarbamate (7.8 g) was added and the solution stirred at room temperature for 12 hours. Diethyl ether/H2O (1:1 500 ml) added and the organic phase separated, dried with MgSO4 and evaporated to a gum. Purification by flash chromatography (dichloromethane: methanol: 880 NH3 (aq) 98.5:1:0.5) gave the sub-title product (10 g).

Workup

  1. customthe organic phase separated
  2. dry with materialdried with MgSO4
  3. customevaporated to a gum
  4. customPurification by flash chromatography (dichloromethane: methanol: 880 NH3 (aq) 98.5:1:0.5)

Sources & evidence

ORD record
ord-b6cbc81e04614e9785818f367e3a0680
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Linked notes

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