Diisopropylethylamine → N-((R)-5-Bromoindan-2-yl)-4-butoxy-N-methylbenzamide

HRID 1039644Notes

Reaction equation

HRID 1039644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH2:11])[CH2:5]2.[CH:12](N(C(C)C)CC)(C)C.[CH2:21]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH3:24]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([N:11]([CH3:12])[C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([O:25][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:27][CH:28]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1185614-Butoxybenzoyl chlorideHCID 112758701H-Inden-2-amine, 5-bromo-2,3-dihydro-, (2R)-

Product 1

HCID 66679860N-((R)-5-Bromoindan-2-yl)-4-butoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-5-bromoindan-2-ylamine (hydrochloride; 3.50 g), diisopropylethylamine (5.0 ml) and dichloromethane (20 ml) was admixed at 0° C. with 4-butoxybenzoyl chloride (3.00 g). After 30 minutes, the reaction mixture was partitioned between water and dichloromethane. The organic phase was concentrated and the residue was stirred with diethyl ether. The resulting amide was methylated on the amide nitrogen according to method D. This afforded the product with the molecular weight of 402.33 (C21H24BrNO2); MS (ESI): 402 (M+H+).

Workup

  1. customthe reaction mixture was partitioned between water and dichloromethane
  2. concentrationThe organic phase was concentrated
  3. customThis afforded the product with the molecular weight of 402.33 (C21H24BrNO2)

Sources & evidence

ORD record
ord-50aaa5ee56104e12b4c964dbe13c2bee
Source dataset
uspto-grants-2013_10
Patent number
US08552199B2

Reaction notes

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