Hydrochloric Acid → 3-Amino-1-morpholin-4-ylpropan-1-one;2-phenylacetic acid

HRID 2222882ノート

反応式

HRID 2222882 の反応式
[NH2:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].Cl.C[O-].[Na+].[C:16]1([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[C:16]1([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 999Phenylacetic AcidHCID 65042503-Amino-1-(morpholin-4-yl)propan-1-oneHCID 10942334Sodium Methoxide

生成物 1

HCID 865859193-Amino-1-morpholin-4-ylpropan-1-one;2-phenylacetic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A reactor is charged with 3-amino-1-morpholin-4-yl-propan-1-one; hydrochloride (765 mmol). MeOH (380 mL) is added, and the mixture is stirred vigorously at room temperature for ca. 10 minutes. MtBE (380 mL) is added and the resulting slurry is cooled to −10° C., where a 25% (w/w) MeOH solution of NaOMe (765 mmol) is added slowly via addition funnel at such a rate as to maintain an internal temperature of ca. −10° C. The resulting suspension is stirred vigorously under a N2 atmosphere as it is allowed to warm to 0° C. Solids are removed via filtration, rinsing with additional MtBE (50 mL). Solvent is removed in vacuo to provide the free base as a crude oil that is taken up in MtBE (600 mL). The mixture is cooled with vigorous agitation to ca. 0° C., where phenylacetic acid (765 mmol) is added slowly as a solution in MtBE (300 mL). The reaction mixture is stirred an additional 10 minutes after complete addition, during which time the product precipitates out of solution. The solids are collected via filtration, washed with additional MtBE (100 mL) and dried under vacuum at ≦40° C. to provide 3-amino-1-morpholin-4-yl-propan-1-one; compound with phenylacetic acid (191 g). This material is carried on to subsequent steps without further purification, or optionally, it can be re-precipitated from MtBE.

後処理

  1. additionMtBE (380 mL) is added
  2. temperaturethe resulting slurry is cooled to −10° C.
  3. temperatureto maintain an internal temperature of ca. −10° C
  4. stirringThe resulting suspension is stirred vigorously under a N2 atmosphere as it
  5. temperatureto warm to 0° C
  6. customSolids are removed via filtration
  7. washrinsing with additional MtBE (50 mL)
  8. customSolvent is removed in vacuo
  9. customto provide the free base as a crude oil that
  10. temperatureThe mixture is cooled with vigorous agitation to ca. 0° C.
  11. stirringThe reaction mixture is stirred an additional 10 minutes
  12. additionafter complete addition
  13. customduring which time the product precipitates out of solution
  14. filtrationThe solids are collected via filtration
  15. washwashed with additional MtBE (100 mL)
  16. customdried under vacuum at ≦40° C.

出典と根拠

ORDレコード
ord-422d6815f27743c495cb2edc875f7f70
出典データセット
uspto-grants-2008_05
特許番号
US07371855B2

反応ノート

読み込み中…