tert-butyl (2S)-2-[(4-{[(3,4-dichlorophenyl)amino]-carbonyl}piperazin-1-yl)methyl]morpholine-4-carboxylate → N-(3,4-Dichlorophenyl)-4-[(2R)-morpholin-2-ylmethyl]piperazine-1-carboxamide

HRID 603200Notes

Reaction equation

HRID 603200 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>FC(F)(F)C(O)=O.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 57656853tert-butyl (2S)-2-[(4-{[(3,4-dichlorophenyl)amino]-carbonyl}piperazin-1-yl)methyl]morpholine-4-carboxylate

Product 1

HCID 57656675N-(3,4-Dichlorophenyl)-4-[(2R)-morpholin-2-ylmethyl]piperazine-1-carboxamideYield 161.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Trifluoroacetic acid/Dichloromethane (20 ml, 1:1) was added to tert-butyl (2S)-2-[(4-{[(3,4-dichlorophenyl)amino]-carbonyl}piperazin-1-yl)methyl]morpholine-4-carboxylate (2.10 g) under argon and stirred for 1 h. The solvent was then removed on a rotavapor and azeotroped (2×20 ml) with toluene and dried for 24 h under high vacuum to afford the title compound (2.67 g) as a brown oil which was used without further purification.

Workup

  1. customThe solvent was then removed on a rotavapor
  2. customazeotroped (2×20 ml) with toluene
  3. customdried for 24 h under high vacuum

Sources & evidence

ORD record
ord-09e9205dbbd24a25b67355fc0915a99e
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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