Water → HCID 15916789, compound

HRID 354670Notes

Reaction equation

HRID 354670 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C-:6]#[N:7].[Na+].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.O>Cl.CO>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[C:6]#[N:7])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 90863-Amino-1-propanolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 15916789HCID 15916789, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

to a cold solution (0° C.) of 30.2 g. of 3-amino-1-propanol dissolved in 161.2 ml of 2.5 N hydrochloric acid, add 19.8 g of sodium cyanide followed by a solution of 50.0 g of 4-fluorobenzaldehyde in 160 ml of methanol. Stir the reaction mixture at room temperature (20° C.) for twenty four (24) hours, then treat with 500 ml of water and extract with ethyl ether. Dry the ether extract over sodium sulfate and concentrate to an oily residue which subsequently crystallizes. Recrystallize from isopropyl ether to obtain thereby the title compound which melts at 69°-70° C.

Workup

  1. customto a cold solution (0° C.) of 30.2 g
  2. extractionextract with ethyl ether
  3. dry with materialDry the ether
  4. extractionextract over sodium sulfate
  5. concentrationconcentrate to an oily residue which
  6. customsubsequently crystallizes
  7. customRecrystallize from isopropyl ether
  8. customto obtain

Sources & evidence

ORD record
ord-d498f950fde14b90b0d37ac7d2e317d9
Source dataset
uspto-grants-1983_03
Patent number
US04376769

Reaction notes

Loading…