Dichloromethane → 4-Amino-4-[(2,4-difluoro-benzoylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 632734Notes

Reaction equation

HRID 632734 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([NH2:16])([CH2:14][NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[F:20][C:21]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([NH2:16])([CH2:14][NH:15][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:21]=2[F:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5880812,4-Difluorobenzoyl chlorideHCID 22975818tert-Butyl 4-amino-4-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 894425284-Amino-4-[(2,4-difluoro-benzoylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-Amino-4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (250 mg; 1.1 mmol; 1.0 eq.) in pyridine (12 ml) at room temperature, a 0.1 M DCM solution of 2,4-difluoro-benzoyl chloride (182.8 mg; 1.04 mmol; 0.95 eq.) was added slowly. The reaction mixture was quenched by adding 0.5 mL of methanol when LC-MS showing no starting material remaining. The reaction mixture and concentrated to dryness to afford 4-Amino-4-[(2,4-difluoro-benzoylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding 0.5 mL of methanol when LC-MS
  3. concentrationThe reaction mixture and concentrated to dryness

Sources & evidence

ORD record
ord-1a02c9e52fbb40a68f6a5c084a8e3f95
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

Loading…