Ammonia → 1-Amino-3-({[4-(aminomethyl)cyclohexyl]methyl}amino)propan-2-ol

HRID 1439777ノート

反応式

HRID 1439777 の反応式
[CH:1]1([CH2:9][NH2:10])[CH2:6][CH2:5][CH:4]([CH2:7][NH2:8])[CH2:3][CH2:2]1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.[OH-].[NH4+:17].C(Cl)C(O)C.N>CO>[NH2:17][CH2:11][CH:13]([OH:15])[CH2:14][NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][NH2:10])[CH2:2][CH2:3]1

参加物

7

反応物 5

HCID 222AmmoniaHCID 7835EpichlorohydrinHCID 14923Ammonium HydroxideHCID 173541,4-CyclohexanedimethanamineHCID 313701-Chloro-2-propanol

生成物 1

HCID 203734301-Amino-3-({[4-(aminomethyl)cyclohexyl]methyl}amino)propan-2-ol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

反応条件

温度
20 °C

実験手順

1,4-Cyclohexanebis(methylamine) (14.2 g., 0.1 mole) is dissolved in 50 ml. of anhydrous methyl alcohol and the solution cooled to +5° C. in an ice bath. Epichlorohydrin (9.3 g., 0.1 mole) is added in a 2-minute period and the temperature maintained at +5° C. for 2 hours; reaction is allowed to continue at 10° C-15° C. until thin layer chromatography of an aliquot (silica gel plate with development using a solution of 1 volume concentrated aqueous ammonium hydroxide in 4 volumes of methyl alcohol) indicated nearly complete conversion of the starting diamine to the propylene chlorohydrin. The solution is then added to 100 ml. of dry methyl alcohol previously saturated at 0° C. with dry ammonia gas by continuous dropwise flow at +5° C. with good agitation and external cooling. After stirring 2 hours at +5° C., it is allowed to warm to 20° C. and mixed overnight. The reaction is completed by heating at 45° C.-55° C. for 6 hours. The solvent and ammonia was removed by stripping and the product purified using fractional distillation under reduced pressure.

後処理

  1. temperaturethe temperature maintained at +5° C. for 2 hours
  2. customreaction
  3. customto continue at 10° C-15° C. until thin layer chromatography of an aliquot
  4. additionThe solution is then added to 100 ml
  5. custompreviously saturated at 0° C.
  6. customat +5° C.
  7. additionmixed overnight
  8. temperatureby heating at 45° C.-55° C. for 6 hours
  9. customThe solvent and ammonia was removed
  10. customthe product purified
  11. distillationdistillation under reduced pressure

出典と根拠

ORDレコード
ord-820bf970b50146d29adc765522830baa
出典データセット
uspto-grants-1977_11
特許番号
US04060639

反応ノート

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