Dichloromethane → HCID 10149879, compound

HRID 2247000Notes

Reaction equation

HRID 2247000 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:13][N:14](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:16][N:8]3[C:9]=2[C:4]=1[CH:5]1[CH2:29][CH2:28][CH2:27][CH:6]1[CH2:7]3.FC(F)(F)S(O)(=O)=O.C1(OC)C=CC=CC=1.[OH-].[Na+].C(Cl)[Cl:51]>O>[ClH:51].[F:30][C:2]([F:1])([F:31])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:13][NH:14][CH2:15][CH2:16][N:8]3[C:9]=2[C:4]=1[CH:5]1[CH2:29][CH2:28][CH2:27][CH:6]1[CH2:7]3

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 7519AnisoleHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 10288018HCID 10288018, compound

Product 1

HCID 10149879HCID 10149879, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing the compound of example 29 (0.345 g, 0.80 mmol) dissolved in methylene chloride (1.2 mL) were added trifluoromethane sulfonic acid (0.496 mL, 5.6 mmol) and anisole (0.261 mL, 2.4 mmol) at room temperature. After 1 hour, the reaction was completed and the reaction mixture was basified to a pH of 12 with 1N NaOH. Water and methylene chloride were added and the reaction mixture was stirred for 45 minutes. The contents of the flask were transferred to a separatory funnel, and the aqueous layer was extracted with methylene chloride (4×). The combined organic layers were dried with magnesium sulfate, filtered and concentrated to give yellow oil. Further purification (10% ammonia in 2M solution of ethanol/Ethyl acetate) yielded 0.190 g of the free amine product (80%). The free amine was then taken and converted into the hydrochloride salt. After the compound was dissolved in diethyl ether, HCl in a 2M solution in diethyl ether (0.32 mL, 0.64 mmol) was added. After the mixture stirred for 30 minutes, the resulting yellow precipitate was filtered off to give 0.1932 g of the desired product.

Workup

  1. customThe contents of the flask were transferred to a separatory funnel
  2. extractionthe aqueous layer was extracted with methylene chloride (4×)
  3. dry with materialThe combined organic layers were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give yellow oil
  7. customFurther purification (10% ammonia in 2M solution of ethanol/Ethyl acetate)

Sources & evidence

ORD record
ord-139d064df94c450580ff5879c2bbda14
Source dataset
uspto-grants-2010_03
Patent number
US07687620B2

Reaction notes

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