Hydrochloric Acid → HCID 67423169, compound

HRID 2365909Notes

Reaction equation

HRID 2365909 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:10])[CH3:7].Cl.[CH2:19]([O:26][C:27]1[CH:32]=[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:28]=1Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.CCCCCC>[CH2:6]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:32][C:31]=2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([OH:17])[CH2:15][CH2:16]1)=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzeneHCID 178418339Butyllithium

Product 1

HCID 67423169HCID 67423169, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

In a 500 ml three-necked flask, 20 g of 2,4-bis(benzyloxy)-1-bromobenzene are dissolved in 240 ml of tetrahydrofuran. The mixture is cooled to −70° C. and then 26 ml of 2.5M n-butyllithium in hexane are added. The reaction medium is stirred at −70° C. for 1 hour, and then 11.1 g of 4-oxo-piperidine-1-carboxylic acid ethyl ester are added dropwise. The reaction medium is stirred at −70° C. for 2 hours and then left at ambient temperature overnight. The reaction medium is poured into 100 ml of a 2M solution of hydrochloric acid and then extracted with 400 ml of ethyl acetate. The organic phases are combined, washed with 150 ml of water and then dried over magnesium sulphate and evaporated.

Workup

  1. stirringThe reaction medium is stirred at −70° C. for 2 hours
  2. waitleft at ambient temperature overnight
  3. extractionextracted with 400 ml of ethyl acetate
  4. washwashed with 150 ml of water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-9841616c2017431bbf398baac7fa3b82
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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