Triphenylphosphine → [2,2-Dimethyl-3-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-propyl]-dimethyl-amine

HRID 2415492Notes

Reaction equation

HRID 2415492 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([OH:17])=[CH:7][CH:8]=2)[N:3]=1.[CH3:18][N:19]([CH3:26])[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(Cl)Cl.CO.[NH4+].[OH-]>[CH3:22][C:21]([CH3:25])([CH2:24][O:17][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)[CH2:20][N:19]([CH3:26])[CH3:18]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 879193-(Dimethylamino)-2,2-dimethyl-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1358041182-Methyl-4-pyrrolidin-1-yl-quinolin-7-ol2×

Product 1

HCID 22641439[2,2-Dimethyl-3-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-propyl]-dimethyl-amineYield 23%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21896990Dichloromethane methanol ammonium hydroxideSolvent

Procedure

A suspension of 114 mg (0.5 mmol) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol, product of example 2, 71 mg (0.53 mmol) of 3-dimethylamino-2,2-dimethyl-1-propanol, 196.7 mg (0.75 mmol) of triphenyl phosphine in THF (4 ml) was treated at RT with 123 μl (0.75 mmol) of diethyl azodicarboxylate and stirred at RT for 48 h. The precipitate that had formed was removed by filtration, the filtrate was concentrated in vacuo and the oily residue obtained was applied to silica gel column with CH2Cl2/MeOH/NH4OH (90:10:1) as eluent. The purified fractions were combined and concentrated in vacuo. The residue was taken up in ether, the crystalline solid that formed was filtered off by suction and dried in a high vacuum to give 24 mg (23%) of the desired [2,2-dimethyl-3-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-propyl]-dimethyl-amine as an off-white solid. ISP mass spectrum, m/e: 342.4 (M+1 calculated for C21H31N3O: 342). (Further material, 30 mg, 29%, was obtained on concentration of the mother liquid and collection of the product as hydrochloride salt).

Workup

  1. customThe precipitate that had formed
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe oily residue obtained
  5. concentrationconcentrated in vacuo
  6. customthe crystalline solid that formed
  7. filtrationwas filtered off by suction
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-259de672192b44f9844b8fba7d869c1d
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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