Diisopropylethylamine → HCID 54529144, compound

HRID 2165173Notes

Reaction equation

HRID 2165173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH2:10]OS(C)(=O)=O)[C:7]=2[CH:16]=1.[CH2:17]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1)=[O:21])[CH3:18].C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH2:17]([O:19][C:20]([CH:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH2:10][C:8]2[C:7]3[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[CH:9]=2)[CH2:23]1)=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98969Ethyl nipecotateHCID 178487221HCID 178487221, compound

Product 1

HCID 54529144HCID 54529144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.27 g (30 mmol) of methanesulphonic acid (5-methoxybenzocyclobuten-1-yl)methyl ester in 60 ml of dimethylformamide there are added first 5.66 g (36 mmol) of piperidine-3-carboxylic acid ethyl ester and then 9.70 g (75 mmol) of N-ethyl-N,N-diisopropylamine. The mixture is stirred at 60° for 18 hours and, after cooling, is concentrated by evaporation under a high vacuum. The residue is taken up in diethyl ether and washed with water, and the organic phase is extracted with 2N hydrochloric acid. The hydrochloric acid extracts are combined, rendered alkaline at reduced temperature with concentrated sodium hydroxide solution and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated to dryness by evaporation under reduced pressure. 1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester is obtained in the form of a yellow oil.

Workup

  1. temperatureafter cooling
  2. concentrationis concentrated by evaporation under a high vacuum
  3. washwashed with water
  4. extractionthe organic phase is extracted with 2N hydrochloric acid
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-10f5987a49424fd6a87f76854771e4ef
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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