Morpholine → HCID 5050621, compound

HRID 892931Notes

Reaction equation

HRID 892931 reaction equation
S([O-])(O)=O.[Na+].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[C-:21]#[N:22].[Na+].[OH-].[Na+]>O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:21]#[N:22])=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 707414-BromobenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 5050621HCID 5050621, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 78.1 parts of sodium hydrogen sulfite in 400 parts of water was stirred for 15 min at 20° C. under a nitrogen atmosphere. After cooling to -5° C., there were added portionwise 100 parts of 4-bromobenzaldehyde and stirring was continued for 20 min at 10° C. Next there were added portionwise 65.3 parts of morpholine and, after stirring for 15 min, a solution of 26.9 parts of sodium cyanide in 90 parts of water. The mixture was stirred for 22 hours at 50° C. and was then treated with 8.7 parts of a sodium hydroxide solution 50%. The product was filtered off, washed with water and dried in vacuo at 50° C., yielding 138.5 parts (98.5%) of α-(4-bromophenyl)-4-morpholineacetonitrile (interm. 44).

Workup

  1. stirringafter stirring for 15 min
  2. stirringThe mixture was stirred for 22 hours at 50° C.
  3. filtrationThe product was filtered off
  4. washwashed with water
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-d811c63f5f9c428b955531e77937ff14
Source dataset
uspto-grants-1992_06
Patent number
US05120845

Reaction notes

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