1,2-Dichloroethane → N-(4-Hydroxymethylbenzyl)-4-pyrrolidin-1-ylbenzamide

HRID 1727255Notes

Reaction equation

HRID 1727255 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=1.ON1C2C=CC=CC=2N=N1.C(Cl)CCl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[OH:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:14][CH:13]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27955154-(Pyrrolidin-1-yl)benzoic acidHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 11312933N-(4-Hydroxymethylbenzyl)-4-pyrrolidin-1-ylbenzamideYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a mixture of 4-pyrrolidin-1-ylbenzoic acid (2.0 g, 10.5 mmol), (4-aminomethylphenyl)methanol (4.3 g, 31.4 mmol), 1-hydroxybenzotriazole (1.7 g, 12.6 mmol), and DMAP (256 mg, 2.1 mmol) in pyridine (50 mL) was added EDC (3.0 g, 15.7 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and an aqueous NaHCO3 solution (50 mL) was added. The mixture was extracted with 5% MeOH in CHCl3 (150 mL×2), and the organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by MPLC on silica gel (3% MeOH in CHCl3) to afford the titled compound (2.56 g, 79%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous NaHCO3 solution (50 mL) was added
  3. extractionThe mixture was extracted with 5% MeOH in CHCl3 (150 mL×2)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by MPLC on silica gel (3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-85c37c4f756146228ac574c6676b7ae2
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

Loading…