Diisopropylethylamine → HCID 18672331, compound

HRID 1058311Notes

Reaction equation

HRID 1058311 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 18672331HCID 18672331, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c6e3801d961f4c4a86bd28132ab8de7c
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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