Phenol → HCID 69518247, compound

HRID 1179984Notes

Reaction equation

HRID 1179984 reaction equation
[CH2:1]([N:8]([CH2:16][CH3:17])[CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=2)=[CH:24][CH:23]=1)=[O:20].C1(O)C=CC=CC=1>ClCCl>[F:37][C:35]([F:36])([F:38])[C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:19]([N:13]3[CH2:12][CH2:11][CH:10]([CH2:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:16][CH3:17])[CH2:15][CH2:14]3)=[O:20])=[CH:23][CH:24]=2)=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 22047686HCID 22047686, compoundHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformate

Product 1

HCID 69518247HCID 69518247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl-ethyl-piperidin-4-ylmethyl-amine (1.42 mmol) was dissolved in dichloromethane. 4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate (1.42 mmol, 0.451 g) (prepared from the corresponding, phenol by conventional methods) was added at room temperature. The reaction mixture was stirred overnight and evaporated to dryness. The crude product was subjected to column chromatography, ethyl acetate/heptane (1:3)→Triethylamine/ethyl acetate 1:9). The fractions containing the title product, was evaporated to dryness and HCl (g) in ethyl acetate was added and stirred for 16 hours. The solution was evaporated to dryness and dried in vacuum for 16 h. to give the title product. (58%, light yellow crystals). HPLC-MS m/z=514.1 (M+1), Rt: 3.27 min.

Workup

  1. additionwas added at room temperature
  2. customevaporated to dryness
  3. additionThe fractions containing the title product
  4. customwas evaporated to dryness and HCl (g) in ethyl acetate
  5. additionwas added
  6. stirringstirred for 16 hours
  7. customThe solution was evaporated to dryness
  8. customdried in vacuum for 16 h.

Sources & evidence

ORD record
ord-8792792569044af3a7b81b3390b5e757
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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