Acetylene → 4-Benzyl-2-iodomethylmorpholine
Reaction equation
C#C.[CH2:3]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH2:16]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I-:28].[Li+]>>[CH2:3]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH2:16][I:28])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Procedure
The starting material for use in processes (a), (b) and (h) in which A is a vinylene radical may be prepared, as described in Example 1, by reaction of 4-benzyl-2-(toluene-p-sulphonyloxymethyl)morpholine and lithium iodide to give 4-benzyl-2-iodomethylmorpholine. This compound is then reacted with triphenyl phosphine to give 4-benzylmorpholin-2-ylmethyl triphenyl phosphonium iodide which is subsequently reacted with a base to form the corresponding phosphorane. This intermediate is reacted in situ with the appropriate substituted benzaldehyde to give 4-benzyl-2-(β-substituted phenylvinyl)-morpholine as a mixture of cis and trans isomers. These isomers are, if necessary, separated by chromatography, or by fractional crystallisation of an acid-addition salt, and if required this N-benzyl derivative is used to form other N-substituted starting materials. Thus reaction with an aryl or optionally substituted alkyl chloroformate gives the corresponding phenoxy- or alkoxy-carbonyl derivative, or reaction with cyanogen bromide gives the corresponding N-cyano derivative.
Workup
- custommay be prepared
Sources & evidence
- ORD record
- ord-2662bb4367e5449bbacc19b3b8bcb25f
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04088814
Reaction notes
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