Hydrochloric Acid → Hydrochloric Acid

HRID 2395828

반응식

HRID 2395828 반응식
C([Cl:5])(=O)CC.[CH3:6][O:7][CH2:8][C:9]1([N:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23](=[O:26])[CH2:24][CH3:25])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:10]1.S1C=CC=C1CCN1CCC(NC2C=CC=CC=2)(COC)CC1.[ClH:56]>CCOCC.C(N(CC)CC)C.C(Cl)Cl>[ClH:5].[CH3:25][CH2:24][C:23]([N:22]([C:9]1([CH2:8][O:7][CH3:6])[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].[ClH:56]

참가 물질

9

반응물 4

HCID 313Hydrochloric Acid2회HCID 41693Sufentanil2회HCID 62324Propionyl chlorideHCID 152954984-(Methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine2회

생성물 2

HCID 313Hydrochloric AcidHCID 18463211164790-60-7

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

Propionyl chloride (1.3 equivalents) was added to a 0.4M methylene chloride solution of 6 in a glass stoppered RB flask at RT. A mild exotherm developed and analysis by LC at the end of 40 minutes showed 90% sufentanil 7 with about 7% starting material 6. About 8% by weight of triethylamine was then added and stirred for another 40 minutes at RT. LC showed 95% product with no trace of starting material 6. The mixture was then quenched with an excess of dilute ammonium hydroxide and the lower methylene chloride layer was separated, washed with water and dried. Evaporation of methylene chloride gave a yellow powder which by LC amounted to 95% sufentanil 7. This was converted to HCl salt by dissolving in ether (250 ml) and stirring with 4N HCl [100 ml]. The precipitated HCl salt was filtered off, washed with ether and air-dried. Recrystallization from water (6 ml for every gm of Sufentanil.HCl) gave sufentanil HCl (19.6 g) as white paste with LC purity of 99.50%. The isolated yield of the pure HCl salt was 85%. H1NMR (CDCl3): δ7.25-6.85 (m,8H), 4.05 (s,2H), 3.35 (s,3H), 3.14-1.56 (m,14H), 0.95 (t,3H).

후처리

  1. customat RT
  2. customat the end of 40 minutes
  3. customThe mixture was then quenched with an excess of dilute ammonium hydroxide
  4. customthe lower methylene chloride layer was separated
  5. washwashed with water
  6. customdried
  7. customEvaporation of methylene chloride
  8. customgave a yellow powder which by LC
  9. filtrationThe precipitated HCl salt was filtered off
  10. washwashed with ether
  11. customair-dried
  12. customRecrystallization from water (6 ml for every gm of Sufentanil

출처 및 근거

ORD 기록
ord-94076dbe99b148209ca5db418832a78b
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05489689

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