Hydrochloric Acid → HCID 86670979, compound

HRID 515349Notes

Reaction equation

HRID 515349 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:9]1[CH:33]=[CH:32][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([NH:28]C(=O)C)=[CH:24][CH:23]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl>C(O)C>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]([CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:12]3[CH:32]=[CH:33][C:9]([C:3]([OH:8])([C:2]([F:35])([F:1])[F:34])[C:4]([F:5])([F:6])[F:7])=[CH:10][CH:11]=3)[CH2:15][CH2:16]2)=[O:21])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670972HCID 86670972, compound

Product 1

HCID 86670979HCID 86670979, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

N-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidine-4-carbonyl)phenyl)acetamide (1.128 mmol, 567 mg) was dissolved in ethanol (20 mL) and 2M hydrochloric acid (56.4 mmol, 28.2 mL) added. The mixture was heated to 100° C. overnight and cooled. The mixture was purified by strong cation exchange column chromatography and concentrated under reduced pressure to afford the title compound (338 mg). MS (ESI) m/z 461.2 [M+H]+

Workup

  1. temperaturecooled
  2. customThe mixture was purified by strong cation exchange column chromatography
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7442002c568b48699d4fd7395454dca8
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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