p-Toluenesulfonic acid → Tampramine

HRID 463028

Reaction equation

HRID 463028 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH2:5][N:6]([C:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[CH:23][N:22]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:27][C:26]2[CH:25]=[CH:24][CH:23]=[N:22][C:21]1=2

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53769600[2-[(3-Amino-2-pyridinyl)[3-(dimethylamino)propyl]amino]phenyl]phenylmethanone

Product 1

HCID 54961Tampramine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

[2-[[3-(Dimethylamino)propyl](3-amino-2-pyridinyl)amino]phenyl]phenylmethanone from Example 21a is refluxed in excess acetic acid or in toluene solution containing a catalytic amount of p-toluene sulfonic acid to give a solution of the title compound.

Sources & evidence

ORD record
ord-e98347ba6d34436bae05b0ae107a8077
Source dataset
uspto-grants-1985_05
Patent number
US04518603

Linked notes

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