Potassium Carbonate → Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine

HRID 272818ノート

反応式

HRID 272818 の反応式
[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][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][S:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CO.N>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][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][S:25][CH2:24][CH2:23]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 21584172Ammonia methanol dichloromethaneHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 230916864-(3-Chloro-propyl)-thiomorpholine

生成物 1

HCID 59837475Dimethyl-{4-[4-(3-thiomorpholin-4-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}amine収率 39.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1000 mg, 4.25 mmol), 4-(3-chloro-propyl)-thiomorpholine (764 mg, 2,13 mmol), DMF (20 ml), and K2CO3 (2.34 g, 17 mmol) were reacted together according to general procedure B. The isolated material was subjected to chromatography on silica, eluant DCM:MeOH:NH3 (95:5:1) to give the title compound (320 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.86 (d, 2H), 3.99 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.79-2.64 (m, 8H), 2.55 (t, 2H), 2.40 (s, 2H), 2.16-2.04 (m, 2H), 2.01-1.82 (m, 4H), 1.97 (s, 6H).

出典と根拠

ORDレコード
ord-8f21ef72450b4ee99703e4fdaebde445
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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