4-Cyclopentylpiperazin-1-amine → HCID 178496661, compound

HRID 1414872Notes

Reaction equation

HRID 1414872 reaction equation
[CH3:1][C@@H:2]1[C@H:33]([OH:34])[C@@H:32]([CH3:35])[C@@H:31]([OH:36])[C@@H:30]([CH3:37])[C@H:29]([O:38][C:39]([CH3:41])=[O:40])[C@H:28]([CH3:42])[C@@H:27]([O:43][CH3:44])[CH:26]=[CH:25][O:24][C@:21]2([CH3:45])[C:22](=[O:23])[C:14]3=[C:15]([O:20]2)[C:16]([CH3:19])=[C:17]([OH:18])[C:12]2=[C:13]3[C:46]([OH:50])=[C:47]([CH:48]=O)[C:10](=[C:11]2[OH:51])[NH:9][C:7](=[O:8])[C:6]([CH3:52])=[CH:5][CH:4]=[CH:3]1.[NH2:53][N:54]1[CH2:59][CH2:58][N:57]([CH:60]2[CH2:64][CH2:63][CH2:62][CH2:61]2)[CH2:56][CH2:55]1>O1CCCC1>[CH3:1][C@@H:2]1[C@H:33]([OH:34])[C@@H:32]([CH3:35])[C@@H:31]([OH:36])[C@@H:30]([CH3:37])[C@H:29]([O:38][C:39]([CH3:41])=[O:40])[C@H:28]([CH3:42])[C@@H:27]([O:43][CH3:44])[CH:26]=[CH:25][O:24][C@@:21]2([CH3:45])[O:20][C:15]3[C:14]([C:22]2=[O:23])=[C:13]2[C:46](/[C:47](=[CH:48]/[NH:53][N:54]4[CH2:55][CH2:56][N:57]([CH:60]5[CH2:64][CH2:63][CH2:62][CH2:61]5)[CH2:58][CH2:59]4)/[C:10](=[C:11]([OH:51])[C:12]2=[C:17]([OH:18])[C:16]=3[CH3:19])[NH:9][C:7](=[O:8])[C:6]([CH3:52])=[CH:5][CH:4]=[CH:3]1)=[O:50]

Participants

4

Reactant 2

HCID 15124854-Cyclopentylpiperazin-1-amineHCID 64384443-Formylrifamycin2×

Product 1

HCID 178496661HCID 178496661, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.01 Mole of 3-formylrifamycin SV is dissolved in tetrahydrofuran and to the obtained solution 0.011 mole of 1-amino-4-cyclopentylpiperazine is added to the reaction mixture at room temperature. After 30 minutes, the reaction is completed since thin layer chromatography of the mixture shows disappearance of the starting 3-formylrifamycin SV. The solvent is then evaporated off and the residue is crystallized from ethyl acetate. The title product, which melts at 179°-80° C, is obtained in a 55% yield.

Workup

  1. additionis added to the reaction mixture at room temperature
  2. customThe solvent is then evaporated off
  3. customthe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-6bbab30ffd06401a954c5c708e81b0d7
Source dataset
uspto-grants-1977_01
Patent number
US04002752

Reaction notes

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