Hydrochloric Acid → Terbinafine Hydrochloride

HRID 1175206

반응식

HRID 1175206 반응식
[CH3:1][C:2]([C:5]#[C:6]/[CH:7]=[CH:8]/[CH2:9][N:10]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12)[CH3:11])([CH3:4])[CH3:3].[ClH:23]>C(C(C)=O)C>[CH3:4][C:2]([C:5]#[C:6]/[CH:7]=[CH:8]/[CH2:9][N:10]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12)[CH3:11])([CH3:1])[CH3:3].[ClH:23]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 1549008Terbinafine

생성물 1

HCID 5282481Terbinafine Hydrochloride수율 75%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
-10 °C

실험 절차

169.9 g (0.420 mol theoretical) crude terbinafine (example 22) is dissolved in 306 ml methyl ethyl ketone (MEK) at 20/25° C.; then 41.3 ml (1 eq.) of 32% aqueous HCl are added dropwise at 20/30° C. Crystallisation of the product takes place during addition. The suspension is stirred for 15 minutes and then concentrated to a small volume under vacuum at 40° C. to azeotropically eliminate the water present, it is subsequently made up twice with MEK and again concentrated to a small volume under vacuum at 40° C. and finally diluted with MEK to restore it to the initial volume. The suspension is then cooled to −10° C. and stirred for 3 hours. The precipitate is filtered, washed with 2×69 ml cold MEK and dried to constant weight under vacuum at 40° C. 103.3 g (0.317 mol, 75% yield) terbinafine hydrochloride are obtained as a white crystalline solid with purity of 99.8% (HPLC A %) and a melting point of 207° C.-208° C.

후처리

  1. customCrystallisation of the product
  2. additionduring addition
  3. concentrationconcentrated to a small volume under vacuum at 40° C.
  4. concentrationagain concentrated to a small volume under vacuum at 40° C.
  5. additionfinally diluted with MEK
  6. stirringstirred for 3 hours
  7. filtrationThe precipitate is filtered
  8. washwashed with 2×69 ml cold MEK
  9. customdried to constant weight under vacuum at 40° C

출처 및 근거

ORD 기록
ord-ca70d0925c354b5e871fa203bad7a681
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838704B2

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