Phentermine → HCID 18977226, compound

HRID 2393760Notes

Reaction equation

HRID 2393760 reaction equation
[CH3:1][C:2]([NH2:11])([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N([CH2:17][CH3:18])CC)C.[C:19]1(C)[CH:24]=C[C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[C:17]1([CH3:18])[C:22]([S:25]([NH:11][C:2]([CH3:1])([CH3:10])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=[CH:19][CH:24]=1

Participants

5

Reactant 3

HCID 4771PhentermineHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 18977226HCID 18977226, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a nitrogen-blanketed solution of 1,1-dimethyl-2-phenyl-ethylamine (3.56 g, 0.019 mol), methylene chloride (CH2Cl2, 20 mL) and triethylamine (Et3N, 8.01 mL, 0.058 mol) was added para-toluenesulfonyl chloride (TsCl, 4.39 g, 0.023 mol). The mixture was stirred at room temperature for 12 hours while monitoring by gas chromatography. The reaction mixture was partitioned between methylene chloride (100 mL) and water (100 mL) and the organic layer was separated and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated to give 5.73 g of N-toluenesulfonyl-1,1-dimethyl-2-phenyl-ethylamine (yield=99%).

Workup

  1. customThe reaction mixture was partitioned between methylene chloride (100 mL) and water (100 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5e094dcbffe74aa6aa0db5ff9727a12f
Source dataset
uspto-grants-1998_09
Patent number
US05808071

Reaction notes

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