3-(Dimethylamino)propyl chloride hydrochloride → 4-(3-(Dimethylamino)propoxy)aniline

HRID 1713691Notes

Reaction equation

HRID 1713691 reaction equation
N1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)CCCC1.Cl.ClCC[CH2:20][N:21]([CH3:23])[CH3:22]>>[CH3:20][N:21]([CH3:23])[CH2:22][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 100584694-(3-(Dimethylamino)propoxy)aniline

Conditions

Temperature
75 °C

Procedure

The title compound is prepared as described in Example 1 for 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine but using 1-chloro-3-dimethylamino-propane hydrochloride. After a 1.3 h stirring at 75° C. (oil bath temperature) and usual work-up, purification of the crude material by silica gel (157 g) column chromatography (CH2Cl2/MeOH, 50/50) provides the title compound as a dark brown oil: ES-MS: 195.0 [M+H]+; Rf=0.13 (CH2Cl2/EtOH, 50/50).

Workup

  1. customThe title compound is prepared
  2. custom(oil bath temperature) and usual work-up, purification of the crude material by silica gel (157 g) column chromatography (CH2Cl2/MeOH, 50/50)

Sources & evidence

ORD record
ord-19851ee47baf42ce818468d5dd78c0f8
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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