Ammonia → [5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amine

HRID 2423845Notes

Reaction equation

HRID 2423845 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:7]([NH2:9])[CH:8]=1.[N:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N>O1CCCC1.ClCCl.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[C:7]([NH:9][CH2:34][C:33]2[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:37][CH:36]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 111838924-(2-(Piperidin-1-yl)ethoxy)benzaldehydeHCID 230875225-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine

Product 1

HCID 57933790[5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)benzyl]amineYield 15.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine (473 mg) and 4-(2-piperidin-1-ylethoxy)benzaldehyde (484 mg) in tetrahydrofuran (6 ml), dichloromethane (4 ml) and acetic acid (4 ml) was added borane-methyl sulfide complex (0.18 ml), and the solution was stirred for 6 hours at room temperature. The solution was neutralized with ammonia solution on an ice bath, extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (132 mg).

Workup

  1. additionwas added borane-methyl sulfide complex (0.18 ml)
  2. extractionextracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-963b8805149b4479a0d07f6822233743
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

Loading…