Phenethylamine → HCID 67512215, compound

HRID 2404439Notes

Reaction equation

HRID 2404439 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:26](CN)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N:35]12[CH2:45]CCN=C1CCCC[CH2:36]2.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[O:64]1CCCC1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[S:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[CH:8]([O:18][CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:36]([N:35]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH3:45])=[O:64]

Participants

8

Reactant 5

HCID 1001PhenethylamineHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66835733HCID 66835733, compound

Product 1

HCID 67512215HCID 67512215, compound

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
125 °C

Procedure

A screw-capped tube is charged with 2-[(3-bromo-phenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (example 27, 400 mg), N-benzylmethylamine (178 μL), 1,8-diazabicyclo(5.4.0)undec-7-ene (100 μL), trans-di-μ-acetatobis[2-(di-o-tolyl-phosphino)benzyl]dipalladium(II) (22 mg), tri-tert-butylphosphonium tetrafluoroborate (17 mg), molybdenum hexacarbonyl (127 mg) and tetrahydrofurane (3 mL). The tube is sealed and heated at 125° C. for 10 min. The reaction was allowed to cool to room temperature and concentrated under reduced pressure. The residue is purified over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5) to afford 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]-N-benzyl-N-methyl-benzamide which is then converted into its oxalate salt in acetone to give 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]-N-benzyl-N-methylbenzamide, oxalate melting at 103° C.

Workup

  1. customThe tube is sealed
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5)

Sources & evidence

ORD record
ord-7f50a2e472704a7ba3f86ad3e033abcb
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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