4-Chlorobenzylamine → HCID 86699769, compound

HRID 515207Notes

Reaction equation

HRID 515207 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH2:11][CH3:12])[C:5]([C:6]([OH:8])=O)=[C:4]([CH2:13][CH3:14])[CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Cl:48][C:49]1[CH:56]=[CH:55][C:52]([CH2:53][NH2:54])=[CH:51][CH:50]=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][CH3:14])[C:5]([C:6]([NH:54][CH2:53][C:52]2[CH:55]=[CH:56][C:49]([Cl:48])=[CH:50][CH:51]=2)=[O:8])=[C:9]([CH2:11][CH3:12])[CH:10]=1

Participants

6

Reactant 4

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 532567664-Bromo-2,6-diethylbenzoic acid

Product 1

HCID 86699769HCID 86699769, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-2,6-diethyl-benzoic acid (0.30 g, 1.20 mmol) in dichloromethane (3.6 ml) are added diisopropylethylamine (0.58 ml, 3.56 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.54 g, 1.42 mmol) at 0° C. and the mixture is stirred for 20 min followed by the addition of 4-chloro-benzyl amine (0.17 ml, 1.42 mmol). The resulting mixture is stirred at room temperature for 16 h. After completion of the reaction (monitored by TLC) the reaction mixture is diluted with dichloromethane (20 ml) and washed with water (30 ml). The organic layer is dried over sodium sulfate and concentrated in vacuo. The resulting crude product is purified column chromatography (silica gel, 25% ethyl acetate/hexane) to obtain 4-bromo-N-[(4-chlorophenyl)-methyl]-2,6-diethyl-benzamide (0.34 g, 0.90 mmol, 75%).

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 16 h
  2. customAfter completion of the reaction (monitored by TLC) the reaction mixture
  3. washwashed with water (30 ml)
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product is purified column chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2bd3db6f84ce4785a4222e22be91afa1
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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