Hydrochloric Acid → HCID 23024622, compound

HRID 600122Notes

Reaction equation

HRID 600122 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:7])[CH2:5][NH2:6].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=O.[B-][C:17]#[N:18].[Na+]>CO>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][N:2]([CH2:12][C:11]1[CH:10]=[CH:9][CH:14]=[CH:17][N:18]=1)[CH2:3][CH:4]([OH:7])[CH2:5][NH:6][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 142732-PyridinecarboxaldehydeHCID 611571,3-Diamino-2-propanolHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 23024622HCID 23024622, compoundYield 25,746.699%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After concentrated hydrochloric acid (60 mL) was added to a solution of 1,3-diaminopropan-2-ol (32.6 g, 362 mmol) in methanol (2400 mL) and further 2-pyridine aldehyde (116.3 g, 1.09 mmol) was added dropwise, sodium cyanotrihydroborate (50.16 g, 798 mmol) was added. After the completion of the addition, reaction was carried out at room temperature for 3 days. After concentrated hydrochloric acid was added to the reaction solution to adjust pH to 6, the solution was concentrated to a proper extent and a 0.1 N aqueous sodium hydroxide solution was added to adjust pH to 7 and the solution was extracted using chloroform. The obtained chloroform phases were collected and dried and thereafter concentrated. The obtained residue was refined by silica gel column chromatography to obtain 34 g of an aimed product.

Workup

  1. additionwas added dropwise
  2. additionAfter the completion of the addition, reaction
  3. concentrationthe solution was concentrated to a proper extent
  4. additiona 0.1 N aqueous sodium hydroxide solution was added
  5. extractionthe solution was extracted
  6. customThe obtained chloroform phases were collected
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-251a097b51c349ffb939495a8ed9a5c3
Source dataset
uspto-grants-2011_03
Patent number
US07901559B2

Reaction notes

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