5-Bromosalicylaldehyde → HCID 67025664, compound

HRID 2390542Notes

Reaction equation

HRID 2390542 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:11][C@@H:12]1[CH2:17][NH:16][CH2:15][C@H:14]([CH3:18])[NH:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH2:7][N:16]2[CH2:15][C@@H:14]([CH3:18])[NH:13][C@@H:12]([CH3:11])[CH2:17]2)[CH:9]=1

Participants

5

Reactant 3

HCID 728635-BromosalicylaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 67025664HCID 67025664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-2-hydroxybenzaldehyde (1 g, 4.97 mmol) in DCM (50 mL) was added (2R,6S)-2,6-dimethylpiperazine (0.852 g, 7.46 mmol). The mixture was allowed to stir at RT for 40 min before sodium triacetoxyborohydride (1.582 g, 7.46 mmol) was added. The reaction was stirred at RT for 24 h. The mixture was diluted with DCM and washed with sat. NaHCO3 (aq), dried (MgSO4) and evaporated to give a white foam. This was purified by Biotage (eluent=2.5% 7M ammonia in methanol/DCM) to give the sub-title compound as a white solid. Yield: 1.32 g

Workup

  1. additionwas added
  2. washwashed with sat. NaHCO3 (aq)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a white foam
  6. customThis was purified by Biotage (eluent=2.5% 7M ammonia in methanol/DCM)

Sources & evidence

ORD record
ord-197e62fd71b8466cb9999e0cd0b839bb
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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