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

HRID 1394042Notes

Reaction equation

HRID 1394042 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 then added and the solution stirred at room temperature for 24 hrs. The solvent was evaporated and the resulting solid dissolved in ethyl acetate and water were added, the organic phase separated, dried, filtered and evaporated to a solid (17.51 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting solid dissolved in ethyl acetate
  3. additionwater were added
  4. customthe organic phase separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated to a solid (17.51 g)

Sources & evidence

ORD record
ord-35410acc4b7f492e9f096fdc6169d824
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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