1-Bromopropane → HCID 19081885, compound

HRID 963368Notes

Reaction equation

HRID 963368 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:4]([O:19][CH3:20])[CH:3]=1.C(N(CC)CC)C.Br[CH2:29][CH2:30][CH3:31]>CN(C=O)C>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:29][CH2:30][CH3:31])[CH2:16][CH2:17]2)=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 8471TriethylamineHCID 9882676HCID 9882676, compound

Product 1

HCID 19081885HCID 19081885, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Amino-5-chloro-2-methoxyphenyl)-3-(piperidin-4-yl)propan-1-one (0.2 g, 0.67 mmol), prepared as in Example 3 or Example 7, triethylamine (0.2 mL), and 1-bromopropane (0.065 mL, 0.75 mmol) were dissolved in DMF (4 mL) and the solution was stirred at room temperature for 12 hours. The solution was partitioned between aqueous ammonium hydroxide and ethyl acetate. The ethyl acetate layer was separated, washed with water and then brine, dried over sodium sulfate, and evaporated. Purification of the residue by silica gel chromatography (10% CH3OH--CH2Cl2) gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(1-(prop-1-yl) piperidin-4-yl]propan-1-one which was then dissolved in ethanolic hydrochloric acid. Crystallization with ether gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-[1-(prop-1-yl) piperidin-4-yl]propan-1-one hydrochloride (0.15 g, 0.4 mmol), m.p. 200°-201° C.

Workup

  1. customThe solution was partitioned between aqueous ammonium hydroxide and ethyl acetate
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. customevaporated
  6. customPurification of the residue by silica gel chromatography (10% CH3OH--CH2Cl2)

Sources & evidence

ORD record
ord-aab119aa8da243bab8696718131f49fd
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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