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

HRID 968756Notes

Reaction equation

HRID 968756 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=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][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]propylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1 Step (b) (10 g) was dissolved in DMF (50 ml) and triethylamine (14.8 ml) was added. tert-Butyl 3-bromopropylcarbamate (10 g) was added and the solution 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 separated, dried with MgSO4 and evaporated to 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 separated
  5. dry with materialdried with MgSO4
  6. customevaporated to a solid (17.51 g)

Sources & evidence

ORD record
ord-671e89ec0b8c4549b0c8af6055249e7f
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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