Water → HCID 86746846, compound

HRID 248849Notes

Reaction equation

HRID 248849 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17]Cl)[CH3:15])[CH2:3]1.O.C(=O)([O-])[O-].[K+].[K+].[N-:26]=[N+:27]=[N-:28].[Na+]>O1CCCC1>[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([CH:8]([CH3:10])[CH3:9])[C@H:4]([O:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][N:26]=[N+:27]=[N-:28])[CH3:15])[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 57112993HCID 57112993, compound

Product 1

HCID 86746846HCID 86746846, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.5 g of N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)ethyl]-N-(2-chlo roethyl)-N-methylamine were added to a mixture of 40 ml water and 20 ml tetrahydrofuran. 2 g of potassium carbonate and 1 g of sodium azide were added to the mixture. The reaction solution was then stirred at room temperature for 8 hours. The reaction solution was worked up by concentrating to about 30 ml and extracting the aqueous phase with ethyl acetate. After concentration of the ethyl acetate extract, 4.5 g of crude N-[2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-ylo xy)ethyl]-N-(2-azidoethyl)-N-methylamine were obtained, which was used in the next step without further purification.

Workup

  1. concentrationby concentrating to about 30 ml
  2. extractionextracting the aqueous phase with ethyl acetate
  3. extractionAfter concentration of the ethyl acetate extract

Sources & evidence

ORD record
ord-23cdd97c20964c338e085da174d3245e
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Reaction notes

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