3-Methoxypropylamine → 3-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

HRID 217785

反応式

HRID 217785 の反応式
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)(=O)=O.[CH3:16][O:17][CH2:18][CH2:19][CH2:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][NH:21][CH2:20][CH2:19][CH2:18][O:17][CH3:16])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 196884663-(4-Bromophenyl)propyl methanesulphonate2 回

生成物 1

HCID 666785803-(4-bromophenyl)-N-(3-methoxypropyl)propan-1-amine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

3-(4-bromophenyl)propyl methanesulfonate (418 g) and acetonitrile (2 L) were charged into reactor 1. 3-methoxypropylamine (305 g) and potassium carbonate (394 g) were added to reactor 1 and the mixture was warmed to 80-90° C. for 4-16 h. The mixture was analysed for completion (3-(4-bromophenyl)propyl methanesulfonate <0.5%). The reaction was cooled to 25° C. and the suspension was filtered to remove the white solids. The filtrate was concentrated to dryness on a rotary evaporator. The crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L) were charged into reactor 2. After phase separation, the organic layer was collected and washed with 1N HCl (2 L) until pH=4-5. After phase separation, the aqueous phase was basified by 2.5N NaOH solution to pH=9-10 and the resulting aqueous solution was used in the next step without further treatment.

後処理

  1. temperatureThe reaction was cooled to 25° C.
  2. filtrationthe suspension was filtered
  3. customto remove the white solids
  4. concentrationThe filtrate was concentrated to dryness on a rotary evaporator
  5. customThe crude product from the rotary evaporator, MTBE (2 L) and water (1.5 L)
  6. additionwere charged into reactor 2
  7. customAfter phase separation
  8. customthe organic layer was collected
  9. washwashed with 1N HCl (2 L) until pH=4-5
  10. customAfter phase separation

出典と根拠

ORDレコード
ord-a183de74b8264e66a58fed0d0b7f9435
出典データセット
uspto-grants-2012_06
特許番号
US08198285B2

関連ノート

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