Water → HCID 57017083, compound

HRID 361711Notes

Reaction equation

HRID 361711 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][C:11]=1[CH2:21][CH2:22][CH2:23][OH:24])[CH3:5].[CH3:25]I.O>O1CCCC1>[CH3:3][N:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][C:11]=1[CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53892805HCID 53892805, compound

Product 1

HCID 57017083HCID 57017083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (51 mg) was added portionwise over a period of 5 minutes to a stirred solution of N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine (330 mg) in tetrahydrofuran (8 ml) at a temperature of 0° C. and under an atmosphere of argon. The reaction mixture was allowed to warm to 25° C. and stirred for a further 0.5 hour. The reaction mixture was cooled to 0° C. and methyl iodide (0.4 ml) added. The reaction mixture was allowed to warm to 25° C. and the reaction mixture was stirred for a further 15 hours. The reaction mixture was poured into water (15 ml) and extracted with ethyl acetate (4×15 ml). The ethyl acetate extracts were combined, washed with water (10 ml), dried (MgSO4) and evaporated to give a yellow oil. The oil was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 75:25:0.2 mixture of ethyl acetate, hexane, and triethylamine as eluent to give N,N-dimethyl-3-[4-butoxy-2-(3-methoxypropyl)phenoxy]propylamine as a yellow oil (70 mg), NMR ([CD3 ]2SO): 0.92(3H,t), 1.42(2H,m), 1.70(4H,m), 2.1(2H,m), 2.5(6H,s), 2.9(2H,m) and 3.2(3H,s), 3.31(2H,t), 3.9(4H,m), 6.7(2H,s), and 6.82(1H,d); m/z 324 (M+H). The N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine used as starting material was prepared as follows.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureto warm to 25° C.
  3. stirringthe reaction mixture was stirred for a further 15 hours
  4. extractionextracted with ethyl acetate (4×15 ml)
  5. washwashed with water (10 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a yellow oil
  9. customThe oil was purified by flash column chromatography on silica gel (Merck Art No 9385)
  10. additiona 75:25:0.2 mixture of ethyl acetate, hexane, and triethylamine as eluent

Sources & evidence

ORD record
ord-f2cac3d6940845d0866b2bc1d7315a20
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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