Dimethylformamide → HCID 59837390, compound

HRID 272822Notes

Reaction equation

HRID 272822 reaction equation
[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][CH:25]([OH:28])[CH2:24][CH2:23]1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH3:3][N:2]([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][CH:25]([OH:28])[CH2:24][CH2:23]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)[CH3:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127257181-(3-Chloropropyl)piperidin-4-olHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 59837390HCID 59837390, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (500 mg, 2.13 mmol), 1-(3-chloro-propyl)-piperidin-4-ol (378 mg, 2,13 mmol), DMF (10 ml) and K2CO3 (1.18 g, 8.52 mmol) were reacted together according to general procedure B. The isolated material was dissolved in EtOAc (30 ml), washed with NaOH (2M, 2×20 ml) and water (25 ml), dried over MgSO4 filtered and concentrated in vacuo at 35° C. to give the title compound (411 mg, 51%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 4.00 (t, 2H), 3.80-3.65 (m, 3H), 3.55 (td, 2H), 2.85-2.73 (m, 2H), 2.52 (t, 2H), 2.40 (s, 2H), 2.22-1.82 (m, 10H), 1.97 (s, 6H), 1.66-1.54 (m, 2H), 1.52 (br s, 1H).

Workup

  1. washwashed with NaOH (2M, 2×20 ml) and water (25 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo at 35° C.

Sources & evidence

ORD record
ord-3bb3f1cb5e304eb9b0eb194e0d130abb
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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