Dichloromethane → Ammonium Hydroxide

HRID 271382Notes

Reaction equation

HRID 271382 reaction equation
C(OCC)(=[O:3])C.[C:7]1([CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH:19]([N:22]=[N+]=[N-])[CH2:18][CH:17]2[F:25])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)Cl>[Pd].CO>[OH-:3].[NH4+:22].[F:25][CH:17]1[CH:16]([O:15][CH2:14][CH2:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 725741444-Azido-2-fluorocyclohexyl 2-phenylethyl ether

Product 2

HCID 14923Ammonium HydroxideHCID 69276156[3-Fluoro-4-(2-phenylethoxy)cyclohexyl]amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To an ethyl acetate (80 mL) solution of 4-Azido-2-fluorocyclohexyl 2-phenylethyl ether (0.677 g, 2.57 mmol) was added 10% palladium on carbon (0.200 g). The resulting mixture was hydrogenated using a balloon. After 1 h the contents of the reaction flask were filtered through Celite® and the filtrate evaporated under reduced pressure. Flash column chromatography (methylene chloride:methanol:ammonium hydroxide, 90:10:1) gave [3-Fluoro-4-(2-phenylethoxy)cyclohexyl]amine as a waxy oil (0.519 g, 85% yield).

Workup

  1. filtrationAfter 1 h the contents of the reaction flask were filtered through Celite®
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-55e5248c1ccf43db90af744311a51c78
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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