Benzenemethanamine, 3-chloro- → HCID 54004440, compound

HRID 1956693Notes

Reaction equation

HRID 1956693 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:24]([O:28][C:29]([NH:31][C@@H:32]([CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:33]=O)=[O:30])([CH3:27])([CH3:26])[CH3:25].C([O-])(O)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[C:24]([O:28][C:29]([NH:31][C@@H:32]([CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH2:33][NH:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 77802Benzenemethanamine, 3-chloro-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10355503HCID 10355503, compound

Product 1

HCID 54004440HCID 54004440, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chlorobenzylamine (0.628 mL, 5.14 mmol) and crushed molecular sieves (1.5 g) in dichloroethane (10 mL) under nitrogen at 0° C. was added sodium triacetoxyborohydride (2.73 g, 12.9 mmol), followed the product from Step C (2.73 g, 5.14 mmol). The reaction was stirred overnight, allowing it to warm to room temperature. The solution was poured into EtOAc and sat NaHCO3 solution, and the organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product which was purified by silica gel chromatography (2.5-5% MeOH/CHCl3) to obtain the titled compound (1.53 g) as a white foam.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product which
  6. customwas purified by silica gel chromatography (2.5-5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-6ec60d1951a0464fba53fdbe3aff0558
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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