Hydrochloric Acid → HCID 86598843, compound

HRID 221206Notes

Reaction equation

HRID 221206 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(N(CC)CC)C.Cl>O1CCCC1>[F:18][C:2]([F:1])([F:17])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([NH:16][S:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:31])[F:32])=[CH:26][CH:25]=3)(=[O:29])=[O:28])=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 18943538HCID 18943538, compound

Product 1

HCID 86598843HCID 86598843, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g (2.68 mmol) of 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-amine and 947 mg (3.87 mmol) of 4-(trifluoromethyl)benzenesulfonyl chloride were dissolved in 20 ml of tetrahydrofuran at room temperature, and 1.62 ml (11.62 mmol) of triethylamine were added dropwise to the solution, which was stirred at room temperature overnight. After evaporation of the solvent, 20 ml of water were added and acidified with 1 mol of hydrochloric acid, and the aqueous phase was extracted with 50 ml of diethyl ether. The residue obtained after drying with sodium sulfate and after removal of the solvent was separated by column chromatography (cyclohexane/ethyl acetate 6:1).

Workup

  1. customAfter evaporation of the solvent, 20 ml of water
  2. additionwere added
  3. extractionthe aqueous phase was extracted with 50 ml of diethyl ether
  4. customThe residue obtained
  5. dry with materialafter drying with sodium sulfate
  6. customafter removal of the solvent
  7. customwas separated by column chromatography (cyclohexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-8ab98ca6dad843e9a9ab0576dcf13d50
Source dataset
uspto-grants-2012_06
Patent number
US08207160B2

Reaction notes

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