Dimethylformamide → Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 484485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 484485
[BH4-].[Na+].CN(C)C=O.Cl[C:9](=[O:28])[CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1>O>[OH:28][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 12674069(Phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate

Produkt 1

HCID 14989193Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylateAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred and cooled (ice bath, 10° C.) mixture of 3.4 parts of sodium tetrahydroborate and 188 parts of N,N-dimethylformamide were added dropwise 28 parts of (phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate (exothermic reaction, the temperature rose to 38° C.). Upon completion addition, the reaction mixture was stirred over weekend at room temperature. The reaction mixture was poured into water and the product was extracted with methylbenzene. The extract was dried, filtered and evaporated, yielding 15.4 parts (61.6%) of (phenylmethyl) 4-(3-hydroxypropyl)-1-piperidinecarboxylate as a residue (int. 35).

Aufarbeitung

  1. temperaturecooled
  2. customexothermic reaction
  3. customrose to 38° C.
  4. additionUpon completion addition
  5. stirringthe reaction mixture was stirred over weekend at room temperature
  6. extractionthe product was extracted with methylbenzene
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e5fbd2d085b84ab38a8b8d7eecf78437
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231184

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