Acetic Acid → HCID 18671477, compound

HRID 1057493Notes

Reaction equation

HRID 1057493 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:10][CH2:11][CH2:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 90863-Amino-1-propanolHCID 811292-BromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18671477HCID 18671477, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirring solution of 2-bromobenzaldehyde in dichloroethane (0.4 M) at RT under nitrogen was added 3-aminopropanol (1.5 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (4 eq). After 5 hr the reaction was carefully quenched with 2M sodium carbonate and extracted with methylene chloride. The organic phase was extracted with 1N hydrochloric acid. The aqueous phase was neutralized with 1N sodium hydroxide and extracted with methylene chloride. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. EI-MS m/z 245 (M+H)+

Workup

  1. customAfter 5 hr the reaction was carefully quenched with 2M sodium carbonate
  2. extractionextracted with methylene chloride
  3. extractionThe organic phase was extracted with 1N hydrochloric acid
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford the product

Sources & evidence

ORD record
ord-b3d335638ba945dd91a1b6c92964c8a2
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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