1-Hydroxybenzotriazole → 4-[4-(phenylmethyl)-1-piperazinyl]-N-[(tetrahydro-2H-pyran-2-yl)oxy]-benzamide

HRID 1798790Notes

Reaction equation

HRID 1798790 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH2:30].ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:30][O:29][CH:24]4[CH2:25][CH2:26][CH2:27][CH2:28][O:23]4)=[O:19])=[CH:21][CH:22]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 47417244-(4-benzylpiperazin-1-yl)benzoic AcidHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

Product 1

HCID 865980264-[4-(phenylmethyl)-1-piperazinyl]-N-[(tetrahydro-2H-pyran-2-yl)oxy]-benzamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-(phenylmethyl)-1-piperazinyl]-benzoic acid (0.0145 mol), O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (0.029 mol), N,N′-methanetetrayl-biscyclohexanamine (0.0145 mol) and 1-hydroxy-1H-benzotriazole (0.021 mol) in DCM p.a. (200 ml) was stirred at room temperature over the weekend. The reaction mixture was washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from EtOAc, filtered off and dried, yielding 3.5 g and another crop: 2.0 g, total yielding 5.5 g (95%) of 4-[4-(phenylmethyl)-1-piperazinyl]-N—[(tetrahydro-2H-pyran-2-yl)oxy]-benzamide (interm. 8).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was crystallized from EtOAc
  6. filtrationfiltered off
  7. customdried
  8. customyielding 3.5 g

Sources & evidence

ORD record
ord-354cb3c92be94f8ca29d789c50199565
Source dataset
uspto-grants-2013_01
Patent number
US08343988B2

Reaction notes

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