Hydrochloric Acid → 1-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine

HRID 650737노트

반응식

HRID 650737 반응식
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[CH:44][C:43]3[C:38](=[CH:39][C:40]([O:46][CH2:47][CH2:48][N:49]4[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]4)=[CH:41][CH:42]=3)[CH:37]=2)[CH2:9]1)=O)(C)(C)C.Cl>CO>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[O:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:43]([CH:42]=[CH:41][C:40]([O:46][CH2:47][CH2:48][N:49]4[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]4)=[CH:39]3)=[CH:44][CH:45]=2)=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 57227299(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-[2-(4-methyl-piperazin-1-yl)-ethoxy]-naphthalen-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butylester

생성물 1

HCID 98525821-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
50 °C

실험 절차

A solution of 9.15 g (12.14 mmol) (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-[2-(4-methyl-piperazin-1-yl)-ethoxy]-naphthalen-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butylester in 250 ml of methanol was treated at room temperature with 36.41 ml of a 2.0 M solution of hydrogen chloride in methanol and the mixture was stirred at 50° C. for 4 hours. Subsequently, the solution was evaporated under reduced pressure and the residue was partitioned between 200 ml of saturated sodium carbonate solution and 150 ml of methylene chloride. The aqueous phase was again extracted twice with 100 ml of methylene chloride; thereafter the organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 90:10 mixture of methylene chloride and methanol as the eluent resulting in 5.25 g (66% of theory) of 1-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine as an amorphous, colourless solid; MS: 654 (M+H)+.

후처리

  1. customSubsequently, the solution was evaporated under reduced pressure
  2. customthe residue was partitioned between 200 ml of saturated sodium carbonate solution and 150 ml of methylene chloride
  3. extractionThe aqueous phase was again extracted twice with 100 ml of methylene chloride
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe crude product was chromatographed on silica gel using
  8. additiona 90:10 mixture of methylene chloride and methanol as the eluent
  9. customresulting in 5.25 g (66% of theory) of 1-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine as an amorphous, colourless solid

출처 및 근거

ORD 기록
ord-9198737def014c9181ce2d9b43c5c3ec
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274735B1

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