1,2-Dichloroethane → HCID 68499881, compound

HRID 1070749Notes

Reaction equation

HRID 1070749 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:26]1([N:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][CH2:45][NH2:46])[CH2:38][CH2:37]2)[C:35]2[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=2[CH:29]=[CH:28][CH:27]=1>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([NH:46][CH2:45][CH2:44][CH2:43][CH2:42][N:39]2[CH2:40][CH2:41][N:36]([C:26]3[C:35]4[CH2:34][CH2:33][CH2:32][CH2:31][C:30]=4[CH:29]=[CH:28][CH:27]=3)[CH2:37][CH2:38]2)=[O:11])[CH:2]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 69686828HCID 69686828, compound

Product 1

HCID 68499881HCID 68499881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.6 g (11.1 mmol) 3-(3-pyridyl)-acrylic acid and 6.2 ml (44.3 mmol) TEA are suspended in 80 ml absolute dichloromethane and cooled to ca. 0° C. under moisture exclusion. 2.0 g (12.1 mmol) 81% HOBT and 2.3 g (12.1 mmol) EDC are added and the mixture is stirred for 30 min under ice cooling. 4.0 g (10.1 mmol) 4-[4-(5,6,7,8-tetrahydro-naphthalin-1-yl)-piperazin-1-yl]-butylamine are added and the mixture is stirred without cooling overnight at RT. Subsequently, the batch is washed twice with 25 ml 2M sodium hydroxide solution and 25 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically pre-purified over silica gel with CHCl3/CH3OH (95/5) and crystallized twice from acetonitrile (25 ml and 15 ml): Colorless crystals of MP. 108-109° C.; yield 2.7 g (64%).

Workup

  1. stirringthe mixture is stirred
  2. temperaturewithout cooling overnight at RT
  3. washSubsequently, the batch is washed twice with 25 ml 2M sodium hydroxide solution and 25 ml water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe residue is chromatographically pre-purified over silica gel with CHCl3/CH3OH (95/5)
  7. customcrystallized twice from acetonitrile (25 ml and 15 ml)
  8. customcrystals of MP. 108-109° C.

Sources & evidence

ORD record
ord-be9cfcd0fd9743c0871c9db3eb683724
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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