Cycloheptanecarbonyl chloride → N-(Chroman-2-yl)methyl-cycloheptanecarboxamide

HRID 1737944Notes

Reaction equation

HRID 1737944 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5]1.[CH:14]1([C:21](Cl)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[O:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH:4]1[CH2:3][NH:2][C:21]([CH:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:22]

Participants

4

Reactant 2

HCID 12556870Cycloheptanecarbonyl chlorideHCID 22145477(3,4-dihydro-2H-1-benzopyran-2-yl)methanamine hydrochloride

Product 1

HCID 21843756N-(Chroman-2-yl)methyl-cycloheptanecarboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.0 g (25 mmol) of 2-aminomethylchroman hydrochloride are dissolved in 50 ml of pyridine; 5.6 g (35 mmol) of cycloheptanecarbonyl chloride are added dropwise to this solution. After 1 hour at 50° C., the mixture is concentrated and the residue is partitioned between water and toluene/ethyl acetate 1:1. The organic phase is filtered over silica gel. The desired product is eluted with toluene/ethyl acetate 5:1. The amide obtained after concentration is further reacted directly.

Workup

  1. concentrationthe mixture is concentrated
  2. customthe residue is partitioned between water and toluene/ethyl acetate 1:1
  3. filtrationThe organic phase is filtered over silica gel
  4. washThe desired product is eluted with toluene/ethyl acetate 5:1

Sources & evidence

ORD record
ord-ef989f37aaed413fb2cdcc49a1ebf13e
Source dataset
uspto-grants-1999_10
Patent number
US05962513

Reaction notes

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