p-Toluenesulfonic acid → α-(3-Fluorophenyl)-4-morpholineacetonitrile

HRID 1763603Notes

Reaction equation

HRID 1763603 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[C-:27]#[N:28].[K+]>C(Cl)Cl.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:27]#[N:28])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 9032Potassium CyanideHCID 680093-Fluorobenzaldehyde

Product 1

HCID 12449502α-(3-Fluorophenyl)-4-morpholineacetonitrile

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

As in Example 35, the following reactions are carried out. m-Fluorobenzaldehyde is reacted with p-toluenesulfonic acid, morpholine and KCN to give α-(m-fluorophenyl)-4-morpholineacetonitrile as crystals (from CH2Cl2 -hexane) m.p. 74°-75° C.

Sources & evidence

ORD record
ord-fe01d12b251740a79f29d3ba35903e99
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

Loading…