Ammonia → HCID 17955453, compound

HRID 2052761Notes

Reaction equation

HRID 2052761 reaction equation
Cl[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[NH3:17]>ClCCl>[CH:5]1[C:4]2[C:9](=[CH:10][C:11]3[C:16]([C:3]=2[CH2:2][NH:17][CH2:2][C:3]2[C:16]4[C:11]([CH:10]=[C:9]5[C:4]=2[CH:5]=[CH:6][CH:7]=[CH:8]5)=[CH:12][CH:13]=[CH:14][CH:15]=4)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 323859-(Chloromethyl)anthracene

Product 1

HCID 17955453HCID 17955453, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9-chloromethyl anthracene (278 mgr, 1.22 mmoles) in dichloromethane (1.5 ml) was bubbled with gaseous ammonia for 10 minutes. More dichloromethane was added, the reaction vessel was tightly closed and the reaction mixture was stirred for two days, at room temperature. Concentration in vacuo and purification of the crude product by flash chromatography afforded 30 mgr (14%) of N,N-di-(9-anthrylmethyl)-amine as yellow solid. 1H NMR (250 MHz, CDCl3): δ 8.48 (2H, s), 8.25-8.10 (4H, m), 8.09-7.80 (4H, m), 7.55-7.25 (8H, m), 4.95 (4H, s), 1.98 (NH, broad) ppm; 13C NMR (62.5 MHz, CDCl3): δ 131.8, 131.3, 130.4, 129.3, 128.4, 126.2, 125.1, 124.2, 45.6 ppm; FTIR: 3317, 3052, 2919, 2846, 1938, 1726, 1620, 1448, 1096, 1030, 891, 738 cm−1. HRMS (MALDI) calcd for C30H23N [M+H+] 398.1903, found 398.1917.

Workup

  1. customthe reaction vessel was tightly closed
  2. concentrationConcentration
  3. customin vacuo and purification of the crude product by flash chromatography

Sources & evidence

ORD record
ord-c50ff03601c54529a64c631fceacfee9
Source dataset
uspto-grants-2008_02
Patent number
US07326510B2

Reaction notes

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