Dimethylformamide → Ammonia

HRID 862465Notes

Reaction equation

HRID 862465 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.O[N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32]C=2N=N1.CN1CC[O:37][CH2:36][CH2:35]1.CN(C=[O:44])C>>[NH3:11].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N+:19]([O-:44])([C:36](=[O:37])[CH2:35][C:30]4[CH:29]=[CH:28][N:24]=[CH:32][CH:31]=4)[CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 124087Desloratadine

Product 2

HCID 222AmmoniaHCID 211984644-(8-CHLORO-5,6-DIHYDRO-11H-BENZO-[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-11-YLIDENE)-1-[(4-PYRIDINYL)ACETYL]-PIPERIDINE N1 OXIDE

Procedure

To a mixture of 0.933 g(3 mmol) of 4-(8-chloro-5,6-dihydro-11H-benzo-[5,6]cyclohepta(1,2-b]pyridin-11-ylidene)-piperidine (product from Preparative Example 1, step G), 0.46 g(3 mmol) of 4-pyridyl acetic acid N-oxide (prepared as described in Preparative Example 8) 1-hydroxybenzotriazole (0.40 g, 3 mmol) in 20 mL of DMF at ~4° C. and under nitrogen atmosphere was added N- methyl morpholine(1.65 mL, 15 mmol) followed by DEC an reaction stirred overnight at room temperature. The volatiles were stripped off and the resulting semi-solid was partitioned between water and EtOAc. The aqueous phase was washed twice with EtOAc. Combined EtOAc fractions were dried over Na2SO4 and concentrated. The crude product was purified via flash chromatography on silica gel (first eluting with 3% and then 5% MeOH saturated with ammonia in CH2Cl2) to give the title compound as a light brown solid(0.2 g mp=128°-130° C. MH+ 446).

Workup

  1. customthe resulting semi-solid was partitioned between water and EtOAc
  2. washThe aqueous phase was washed twice with EtOAc
  3. dry with materialCombined EtOAc fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified via flash chromatography on silica gel (
  6. washfirst eluting with 3%

Sources & evidence

ORD record
ord-5797e7942c4b4ac5a8df945f0b4cf350
Source dataset
uspto-grants-1998_02
Patent number
US05719148

Reaction notes

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