Sodium hydride → HCID 9839928, compound

HRID 1057614Notes

Reaction equation

HRID 1057614 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl[CH2:26][CH2:27][NH2:28]>CCCCC.CN(C=O)C>[CH2:3]([N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH2:26][CH2:27][NH2:28])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 97937372-Chloroethylamine hydrochlorideHCID 113693279-Benzyl-9H-carbazol-4-ol

Product 1

HCID 9839928HCID 9839928, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8003PentaneSolvent

Procedure

Sodium hydride (60% in oil; 0.934 g, 23.36 mmol) is washed three times with pentane. DMF (5 mL) is added, followed by 9-benzyl-9H-Carbazol-4-ol (1.52 g, 5.56 mmol) dissolved in DMF (10 mL) added over 10 min. The mixture is stirred an additional 5 min and then cooled in an ice-water bath. A solution of 2-chloroethylamine hydrochloride (1.29 g, 11.12 mmol) dissolved in DMF (5 mL) is added dropwise over about 5 min. The cooling bath is removed and the mixture is allowed to stir at room temperature over the weekend. Aq. sodium bicarbonate is added and the mixture partitioned between EtOAc, brine, and aq. sodium bicarbonate. The organic layers are dried over MgSO4 and taken to dryness. The residue is chromatographed on silica gel (120 mL) using CH3OH—CH2Cl2 (4/96) to give 1.26 g (72%) of the title compound as a white solid. An aliquot is crystallized from CH2Cl2-EtOAc-hexane; IR (drift) 1597, 1587, 1458, 1441, 1342, 1329, 1269, 1156, 1145, 1110, 1045, 860, 785, 749, 726 cm−1; 1H NMR (CDCl3) δ3.30, 4.29, 5.51, 6.70, 7.00, 7.12, 7.2-7.4, 8.34. Anal. Calcd for C21H20N2O: C, 79.72; H, 6.37; N, 8.85. Found: C, 78.70; H, 6.41; N, 8.70.

Workup

  1. additionadded over 10 min
  2. temperaturecooled in an ice-water bath
  3. additionis added dropwise over about 5 min
  4. customThe cooling bath is removed
  5. stirringto stir at room temperature over the weekend
  6. additionAq. sodium bicarbonate is added
  7. customthe mixture partitioned between EtOAc, brine, and aq. sodium bicarbonate
  8. dry with materialThe organic layers are dried over MgSO4
  9. customThe residue is chromatographed on silica gel (120 mL)

Sources & evidence

ORD record
ord-e76ab48b159d4e0082c6ac847676c78f
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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