Sodium amide → HCID 21503365, compound

HRID 1287985Notes

Reaction equation

HRID 1287985 reaction equation
[NH2-].[Na+].[CH3:3][O:4][C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=1.Cl[CH2:20][CH:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1>C1(C)C(C)=CC=CC=1>[CH3:3][O:4][C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:20][CH:21]3[CH:26]4[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]4)[CH2:22]3)[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 74490Methyl phenothiazin-2-yl etherHCID 13259909HCID 13259909, compound

Product 1

HCID 21503365HCID 21503365, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

19.8 ml of a 50% suspension of sodium amide in xylene were added to a suspension of 68.3 g of 2-methoxyphenothiazine in 700 ml of anhydrous xylene. The mixture was agitated and heated to reflux. After 41/2 hours, 272 ml of an 8.5% solution of 3-chloromethyl-quinuclidine in xylene were added over a period of an hour and reflux was maintained for 16 hours. After cooling to room temperature, the reaction mixture was worked up as in Example 2. After recrystallisation of the crude product in a mixture of ether and isopropyl oxide, 2-methoxy-10-(3-quinuclidinylmethyl)-phenothiazine, m.p. 135°-136° C, was obtained.

Workup

  1. temperatureheated to reflux
  2. temperaturereflux
  3. temperaturewas maintained for 16 hours
  4. customAfter recrystallisation of the crude product
  5. additionin a mixture of ether and isopropyl oxide, 2-methoxy-10-(3-quinuclidinylmethyl)-phenothiazine, m.p. 135°-136° C
  6. customwas obtained

Sources & evidence

ORD record
ord-be446c210e474fa4b22ed2bc98bb5c60
Source dataset
uspto-grants-1976_10
Patent number
US03987042

Reaction notes

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