Morpholine → HCID 44253356, compound

HRID 2036050Notes

Reaction equation

HRID 2036050 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([OH:21])=O)=[CH:16][C:15]=3[C:22]=2[CH3:23])[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[O:21])=[CH:16][C:15]=3[C:22]=2[CH3:23])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 44253223HCID 44253223, compound

Product 1

HCID 44253356HCID 44253356, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[4-(2,6-Dichloro benzyl)-piperazine-1-yl]-4-methyl-benzofuran-2-carboxylic acid (0.07 g, 0.00017 mol) in anhydrous DMF (275 ml) was added diisopropyl ethyl amine (0.08 ml, 0.0005 mol) and morpholine (0.16 ml, 0.00018 mol) under nitrogen atmosphere. The reaction mixture was stirred for 15 minutes, added Py-BOP (0.11 g, 0.0002 mol) and stirred for 1 hour. The completion of the reaction was confirmed by TLC. The reaction mixture was quenched into ice water. The solid separated was filtered. After drying under vacuum, the crude product was isolated as white solid. The crude product was purified by Prep HPLC using a Zorbax C-18 column with mobile phase 0.1% trifluoroacetic acid in water (A)/Acetonitrile (B) with a flow rate of 20 ml/min to yield {5-[4-(2,6-dichlorobenzyl)piperazine-1-yl]-4-methyl-benzofuran-2-yl}-morpholin-4-yl-methanone (35 mg, 43%).

Workup

  1. stirringstirred for 1 hour
  2. customThe reaction mixture was quenched into ice water
  3. customThe solid separated
  4. filtrationwas filtered
  5. customAfter drying under vacuum
  6. customthe crude product was isolated as white solid
  7. customThe crude product was purified by Prep HPLC

Sources & evidence

ORD record
ord-dfe46c274e1444989245ec30de96a2da
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

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