Dimethylamine, hydrochloride → 4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-dimethylaminocarbonylmethyloxy[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidin-4-ol

HRID 242526Notes

Reaction equation

HRID 242526 reaction equation
[C:1]([CH2:4][O:5][C:6]1[C:11]2[CH2:12][C:13](=[CH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][C:27]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)([OH:30])[CH2:26][CH2:25]3)[C:14]3[C:15]([O:20][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[N:16][CH:17]=[CH:18][CH:19]=3)(O)=[O:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:50][N:51](C)[CH2:52]CCN=C=NCC.Cl.CNC>CN(C)C=O.C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:27]2([OH:30])[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][CH:21]=[C:13]3[C:14]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[O:20][C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([O:5][CH2:4][C:1]([N:51]([CH3:52])[CH3:50])=[O:2])[C:11]=4[CH2:12]3)[CH2:25][CH2:26]2)=[CH:36][CH:35]=1

Participants

9

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66758567HCID 66758567, compound

Product 1

HCID 667587194-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-dimethylaminocarbonylmethyloxy[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidin-4-olYield 86%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of product of example 133 (420 mg) in dimethylformamide (17 ml) were added 1-hydroxybenzotriazol hydrate (250 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (310 mg), dimethylamine hydrochloride (270 mg) and triethylamine (0.45 ml), and the mixture stirred at room temperature for 12 hours. Water and chloroform were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure to give the titled compound (380 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fc1e54894f994d6dae467204c48efe19
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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