Piperidine → Benzenamine, 4-[4-(1-piperidinyl)butyl]-, hydrochloride (1:2)

HRID 905653Notes

Reaction equation

HRID 905653 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13](O)=O)=[CH:6][CH:5]=1)([O-])=O.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.CCN=C=NCCCN(C)C.[ClH:33].C1C=CC2N(O)N=NC=2C=1.Cl.C(OCC)(=O)C>CN(C=O)C>[ClH:33].[ClH:33].[N:16]1([CH2:13][CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 797114-(4-Nitrophenyl)butyric acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 68001600Benzenamine, 4-[4-(1-piperidinyl)butyl]-, hydrochloride (1:2)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-nitrophenyl)butanoic acid and piperidine were allowed to undergo the reaction in DMF using WSC hydrochloride and HOBt, subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to reduce the nitro group, and then reduced in the same manner as in Reference Example 2, and the resulting compound was subjected to salt formation using 4 M hydrogen chloride/ethyl acetate solution to obtain 4-(4-piperidin-1-ylbutyl) aniline dihydrochloride. F: 233.

Sources & evidence

ORD record
ord-f30be38d428d48409a69508d4068b516
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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