Hydrochloric Acid → (R)-2,3-Dihydrobenzo[1,4]dioxin-2-yl-[(S*)-3-(4-trifluoromethylphenyl)-piperidin-1-yl]methanone

HRID 2407222Notes

Reaction equation

HRID 2407222 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11](Cl)=[O:12].Cl.[F:15][C:16]([F:30])([F:29])[C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]([N:25]1[CH2:26][CH2:27][CH2:28][C@@H:23]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:15])([F:29])[F:30])=[CH:18][CH:19]=2)[CH2:24]1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 7022160(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chlorideHCID 450738203-(4-(Trifluoromethyl)Phenyl)Piperidine Hydrochloride

Product 1

HCID 66727248(R)-2,3-Dihydrobenzo[1,4]dioxin-2-yl-[(S*)-3-(4-trifluoromethylphenyl)-piperidin-1-yl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chloride (44 mg, 0.22 mmol) was dissolved in DCM (4 ml). 3-(4-Trifluoromethylphenyl)piperidine HCl (51 mg, 0.19 mmol) and triethylamine were added. The mixture was stirred for 1 h, 1 M HCl (2 ml) was added, and the phases were separated. The organic phase was absorbed on silica and the mixture purified by flash chromatography using heptane/EtOAc as eluent. The fractions containing the first eluting diastereomer were collected to yield 21 mg of A11.

Workup

  1. customthe phases were separated
  2. customThe organic phase was absorbed on silica
  3. customthe mixture purified by flash chromatography
  4. additionThe fractions containing the first eluting diastereomer
  5. customwere collected
  6. customto yield 21 mg of A11

Sources & evidence

ORD record
ord-fd32802016f54574b5101f9be5676de5
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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