Triethylamine → 1-(4-Aminophenyl)pyrrolidine-3-carbonitrile

HRID 905659Notes

Reaction equation

HRID 905659 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12](O)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.CS(Cl)(=O)=O.[CH2:21]([N:23](CC)CC)C.[C-]#N.[Na+]>C1COCC1.CN1CCCC1=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([C:21]#[N:23])[CH2:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 120678131-(4-Nitrophenyl)pyrrolidin-3-ol

Product 1

HCID 230715731-(4-Aminophenyl)pyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(4-Nitrophenyl)pyrrolidin-3-ol and methanesulfonyl chloride were allowed to undergo the reaction in THF in the presence of triethylamine. The resulting compound and sodium cyanide were allowed to undergo the reaction in 1-methyl-2-pyrrolidone under heating. The resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain 1-(4-aminophenyl)pyrrolidine-3-carbonitrile. NMR2: 1.48 (9H, s), 3.12-3.19 (2 H, m), 6.46-6.50 (2 H, m).

Workup

  1. temperatureunder heating

Sources & evidence

ORD record
ord-2c6cf2bf89e8424bb62c6bcd5e288171
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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