Ammonium Chloride → HCID 57152468, compound

HRID 2299663Notes

Reaction equation

HRID 2299663 reaction equation
[Cl-].[NH4+].[CH2:3]([N:10]([CH2:25][C@H:26]([OH:35])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][C:20]([N+:22]([O-])=O)=[CH:21][C:13]=2[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.O.[Fe]>[NH2:22][C:20]1[CH:19]=[CH:18][C:14]2[CH2:15][CH2:16][CH2:17][CH:11]([N:10]([CH2:25][C@H:26]([OH:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:12][C:13]=2[CH:21]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57143322HCID 57143322, compound

Product 1

HCID 57152468HCID 57152468, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of powdered iron (160 mg) and ammonium chloride (15 mg) in a mixture of ethanol (6 ml) and water (2 ml) was refluxed, and to this one was dropwise added (2S)-1-[N-benzyl-N-(3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (158 mg) in ethanol (3 ml). After being further refluxed for 1 hour, insoluble materials were filtered off. The filtrate was evaporated in vacuo. The residue was dissolved into a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:1) to give (2S)-1-[N-(3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (122 mg).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter being further refluxed for 1 hour
  3. filtrationinsoluble materials were filtered off
  4. customThe filtrate was evaporated in vacuo
  5. dissolutionThe residue was dissolved into a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate
  6. customAfter separation
  7. washthe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-ccf8611fb1674123adf08fb965e371e5
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

Loading…