Cyclohexanone → N-Cyclohexyl-N-((3-pyridinyl)propyl)benz(cd)indol-2-amine

HRID 1090250Notes

Reaction equation

HRID 1090250 reaction equation
N1C=CC=C(CCCN)C=1.C1(=O)CCCCC1.[BH3-]C#N.[Na+].[CH:22]1([NH:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[N:38]1[C:46]2[C:41]3[C:42](=[CH:47][CH:48]=[CH:49][C:40]=3[C:39]=1S)[CH:43]=[CH:44][CH:45]=2>CO.C(O)C>[CH:22]1([N:28]([CH2:29][CH2:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[C:39]2[C:40]3[CH:49]=[CH:48][CH:47]=[C:42]4[C:41]=3[C:46](=[CH:45][CH:44]=[CH:43]4)[N:38]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 5

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 135575233-(Pyridin-3-yl)propan-1-amineHCID 15035098N-cyclohexyl-3-(3-pyridinyl)propanamineHCID 178527764HCID 178527764, compound

Product 1

HCID 15035102N-Cyclohexyl-N-((3-pyridinyl)propyl)benz(cd)indol-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The reaction of 3-(3-pyridinyl)propanamine and cyclohexanone in methanol in the presence of NaBH3CN leads to the preparation of N-cyclohexyl-3-(3-pyridinyl)propanamine. The latter compound, upon reaction with molar equivalents of benz(cd)indol-2-thiol and mercuric acetate in refluxing ethanol under the conditions of Example 55 leads to the title compound.

Sources & evidence

ORD record
ord-dbe7d8dbca23492c9cf0f90f3e3ca08f
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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