Dimethylformamide → 3-(Dimethylamino)-1-propanol

HRID 2243366Notes

Reaction equation

HRID 2243366 reaction equation
C(C1[CH:26]=[CH:25][C:7]2[NH:8][C:9](C3C4C5C(=CC=CC=5)C(=O)C=4C=CC=3)=[N:10][C:6]=2[CH:5]=1)(O)=O.[O:27]1C[CH2:30][CH2:29][CH2:28]1.[CH3:32][N:33](C)[CH:34]=O.[Cl:37]CCl>>[CH3:7][N:8]([CH3:9])[CH2:30][CH2:29][CH2:28][OH:27].[ClH:37].[CH3:32][N:33]([CH3:34])[CH2:26][CH2:25][CH2:7][N:8]=[C:9]=[N:10][CH2:6][CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 178524153HCID 178524153, compound

Product 2

HCID 766463-(Dimethylamino)-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Procedure

The procedure used in Example 233 is followed, but starting from 500 mg of 4-(5-carboxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one, obtained in stage 1 of Example 241, 261 μl of 3-dimethylaminopropanol, 280 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), 50 mg of N,N-dimethylaminopyridine (DMAP) in a mixture of 4 ml of dichloromethane, 2 ml of tetrahydrofuran and 1 ml of dimethylformamide, for 20 hours at room temperature. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (9/1 by volume) and then dichloromethane and ammonia as a 7N solution in methanol (9/1 by volume), in this way we obtain 582 mg of 4-{5-[(3-dimethylaminopropyl)carbonyloxy]-1H-benzimidazol-2-yl}-9H-fluoren-9-one, in the form of a yellow resin, which is used as it is in the following stage, with the following characteristics:

Sources & evidence

ORD record
ord-c7af855d61f6473788358b5d1b44ad6c
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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