Morpholine → 4-(6-Chloropyridine-3-carbonyl)morpholine

HRID 1969110Notes

Reaction equation

HRID 1969110 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 792226-Chloronicotinic acid

Product 1

HCID 8574994-(6-Chloropyridine-3-carbonyl)morpholineYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-chloro nicotinic acid (1.11 g, 7.04 mmol) in CH2Cl2 at 0 C was added EDCI (2.70 g, 14.08 mmol) and HOBt and then the resulting mixture was stirred for 30 minutes at 0 C. After that, morpholine (2.46 ml, 28.17 mmol) was added, the ice-bath removed and the reaction was done in 15 minutes. Water was added, the mixture was extracted with CH2Cl2, dried over MgSO4 and concentrated to afford 1.55 g of product.

Workup

  1. customthe ice-bath removed
  2. waitthe reaction was done in 15 minutes
  3. additionWater was added
  4. extractionthe mixture was extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-92f34981b2254afe8459f4b58b052c71
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

Loading…