Diisopropylethylamine → HCID 18672331, 화합물

HRID 1058311노트

반응식

HRID 1058311 반응식
CCN(C(C)C)C(C)C.Cl.[OH:11][CH:12]1[CH2:15][NH:14][CH2:13]1.Br[CH2:17][C:18]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:19]=1[C:20]#[N:21]>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:18]([CH2:17][N:14]2[CH2:15][CH:12]([OH:11])[CH2:13]2)=[C:19]([CH:22]=1)[C:20]#[N:21]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 126680522-(Bromomethyl)-5-chlorobenzonitrile

생성물 1

HCID 18672331HCID 18672331, 화합물수율 82.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

DIEA (3.57 mL, 20.50 mmol) was added to a stirred mixture of 3-hydroxyazetidine hydrochloride (1.00 g, 9.11 mmol) and 2-bromomethyl-5-chlorobenzonitrile (2.10 g, 9.11 mmol) in CH2Cl2 (75 mL). After 16 h the reaction mixture was concentrated and the residue was partitioned between ether and 1N HCl. The aqueous layer was washed with ether, made neutral with NaHCO3, saturated with NaCl and extracted into CH2Cl2. The organic layer was dried (Na2SO4) and evaporated to give 5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzonitrile (1.67 g) as a gum: 1H NMR (CDCl3, 400 MHz) δ 3.03 (m, 2H), 3.68 (m, 2H), 4.49 (t, J=6.2 Hz, 1H), 7.46 (d, J=8.6 Hz, 1H), 7.53 (d,d, J=2.2, 6.2 Hz, 1H), 7.60 (d, J=2.0 Hz, 1H).

후처리

  1. concentrationAfter 16 h the reaction mixture was concentrated
  2. customthe residue was partitioned between ether and 1N HCl
  3. washThe aqueous layer was washed with ether
  4. extractionextracted into CH2Cl2
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-c6e3801d961f4c4a86bd28132ab8de7c
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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