Water → (+/-)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic Acid Benzyl Ester

HRID 1349537Notes

Reaction equation

HRID 1349537 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C@H:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C@@H:13]([CH3:21])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:32][N:33]([CH3:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C@H:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:38](=[O:39])[C:37]2[CH:36]=[CH:35][C:34]([N:33]([CH3:32])[CH3:43])=[CH:42][CH:41]=2)[C@@H:13]([CH3:21])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 58859730HCID 58859730, compound

Product 1

HCID 86592021(+/-)-Cis-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-carbamic Acid Benzyl EsterYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis-(2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester (500 mg, 1.68 mmol) in methylene chloride (20 mL) at room temperature was added diisopropylethylamine (542 mg, 749 uL, 4.2 mmol) followed by 4-dimethylaminobenzoyl chloride and stirred at from temperature until no starting material was present. The mixture was poured into water and extracted with ethyl acetate. The extracts were washed with 1 M (aq) NaOH and brine, dried over sodium sulfate, filtered dried and concentrated. The crude residue was purified by silica gel chromatography (100% hexanes to 70% hexanes/30% ethyl acetate gradient) to afford the amide (665 mg, 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with 1 M (aq) NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customdried
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (100% hexanes to 70% hexanes/30% ethyl acetate gradient)

Sources & evidence

ORD record
ord-4f02c29d565240afa8e4ad4dcc6b0703
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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