Triethylamine → HCID 24808562, compound

HRID 76326Notes

Reaction equation

HRID 76326 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17]O)[CH2:6]2.C(N(CC)CC)C.S(Cl)([Cl:29])=O.[OH-].[Na+]>ClCCl.O>[Cl:29][CH2:17][CH2:16][CH2:15][N:14]([CH2:13][C@H:7]1[CH2:6][C:5]2[C:8]1=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium Hydroxide2×HCID 24386Thionyl ChlorideHCID 71766274HCID 71766274, compound

Product 1

HCID 24808562HCID 24808562, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)-amino]-1-propanol (20.8 g, 78.4 mmoles) and triethylamine (11 mL, 78.9 mmoles) in 200 mL of dichloromethane add, at ambient temperature, 8.65 mL of thionyl chloride (157 mmoles). After being in contact for 3 hours at 40° C., hydrolyse the mixture using 150 mL of water and 30 mL of aqueous 1N NaOH solution. Adjust the pH of the aqueous phase to 10 using aqueous 10N NaOH solution and extract with 50 mL of dichloromethane. Combine the organic phases and wash them with saturated aqueous Na2CO3 solution (100 mL), dry them over MgSO4 and carry out drying in vacuo to obtain 19.8 g of a brown oil corresponding to the title compound.

Workup

  1. additionadd, at ambient temperature
  2. extractionextract with 50 mL of dichloromethane
  3. washwash them with saturated aqueous Na2CO3 solution (100 mL)
  4. dry with materialdry them over MgSO4
  5. customcarry out drying in vacuo

Sources & evidence

ORD record
ord-33f4e71057914e1bae017c357732662c
Source dataset
uspto-grants-2014_09
Patent number
US08835627B2

Reaction notes

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