Potassium Carbonate → Dimethyl-{4-[4-(2-methyl-3-pyrrolidin-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine

HRID 272841노트

반응식

HRID 272841 반응식
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].Cl[CH2:19][CH:20]([CH3:27])[CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH:20]([CH3:27])[CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 225682631-(3-Chloro-2-methyl-propyl)-pyrrolidineHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

생성물 1

HCID 59837457Dimethyl-{4-[4-(2-methyl-3-pyrrolidin-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-amine수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (0.91 g, 3.87 mmol), 1-(3-chloro-2-methyl-propyl)-pyrrolidine (500 mg, 3.10 mmol), DMF (5 ml) and K2CO3 (2.14 g, 15.50 mmol) were reacted together according to general procedure B. The organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. The crude material was subjected to chromatography on silica eluting with DCM:MeOH:NH3 (97:2:1) to provide the title compound (464 mg, 42%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.88 (d, 2H), 4.00 (dd, 1H), 3.80-3.70 (m, 3H), 3.55 (td, 2H), 2.59-2.43 (m, 5H), 2.40 (s, 2H), 2.33 (dd, 1H), 2.21-2.04 (m, 3H), 1.97 (s, 6H), 1.88 (ddd, 2H), 1.82-1.70 (m, 4H), 1.08 (d, 3H).

후처리

  1. washThe organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C

출처 및 근거

ORD 기록
ord-773dec00405d4414941e9447ac992232
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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